Synthesis of enantioenriched tertiary boronic esters from secondary allylic carbamates. Application to the synthesis of C30 botryococcene.

No abstract is available for this paper.

• Publication year

  2012

• Venue

  Journal of the American Chemical Society

• Publication date

  2012-04-23

• Fields of study

  Medicine, Chemistry

• Identifiers
  DOI 10.1021/ja303022dPMID 22524150
• External record

  Open on Semantic Scholar

• Source metadata

  Semantic Scholar, PubMed

• No claims are published for this paper.

• No concepts are published for this paper.

• Erratum: Synthesis of enantioenriched tertiary boronic esters from secondary allylic carbamates. Application to the synthesis of C30 botryococcene (Journal of the American Chemical Society (2012) 134 (7570-7575) DOI: 10.1021/ja303022d)

  2012cited by this paper
• Enantioselective construction of quaternary stereogenic centers from tertiary boronic esters: methodology and applications.

  2011cited by this paper
• Highly enantioselective synthesis of tertiary boronic esters and their stereospecific conversion to other functional groups and quaternary stereocentres.

  2011cited by this paper
• Construction of asymmetric quaternary carbon centers with high enantioselectivity.

  2011cited by this paper
• Enantioselective formal hydration of α,β-unsaturated acceptors: asymmetric conjugate addition of silicon and boron nucleophiles.

  2011cited by this paper
• Identification of unique mechanisms for triterpene biosynthesis in Botryococcus braunii

  2011cited by this paper
• Asymmetric Addition of Diorganozinc Reagents to Aldehydes and Ketones

  2011cited by this paper
• Arylation and Alkenylation of Carbonyl and Imino Groups

  2011cited by this paper
• Enantioselective synthesis of boron-substituted quaternary carbons by NHC-Cu-catalyzed boronate conjugate additions to unsaturated carboxylic esters, ketones, or thioesters.

  2010cited by this paper
• Enantioselective synthesis of allylboronates bearing a tertiary or quaternary B-substituted stereogenic carbon by NHC-Cu-catalyzed substitution reactions.

  2010cited by this paper
• Full chirality transfer in the conversion of secondary alcohols into tertiary boronic esters and alcohols using lithiation-borylation reactions.

  2010cited by this paper
• Conjugate boration of β,β-disubstituted unsaturated esters: asymmetric synthesis of functionalized chiral tertiary organoboronic esters.

  2010cited by this paper
• Copper(I)-secondary diamine complex-catalyzed enantioselective conjugate boration of linear β,β-disubstituted enones.

  2010cited by this paper
• Catalytic Asymmetric Epoxidation of Allylic Alcohols

  2010cited by this paper
• Homologation of boronic esters with lithiated epoxides for the stereocontrolled synthesis of 1,2- and 1,3-diols and 1,2,4-triols.

  2009cited by this paper
• Enantiodivergent conversion of chiral secondary alcohols into tertiary alcohols

  2008cited by this paper
• Enantioselective hydrolysis of 1-arylallyl acetates catalyzed by Candida antarctica lipase

  2008cited by this paper
• Lithiated carbamates: chiral carbenoids for iterative homologation of boranes and boronic esters.

  2007cited by this paper
• Enantiomerically enriched allylic alcohols and allylic amines via C-C bond-forming hydrogenation: asymmetric carbonyl and imine vinylation.

  2007cited by this paper
• Catalytic Asymmetric Synthesis of Allylic Alcohols via Dynamic Kinetic Resolution

  2007cited by this paper
• Asymmetric Homoaldol Reactions with Cyclohex‐2‐enyl N,N‐Diisopropylcarbamate: Kinetic Resolution, Elucidation of the Stereochemical Course and Applications in the Synthesis of Hexahydroisobenzofuran‐4‐(1H)‐ones

  2007cited by this paper
• Iterative stereospecific reagent-controlled homologation of pinacol boronates by enantioenriched alpha-chloroalkyllithium reagents.

  2007cited by this paper
• Synthesis of (S)-(-)-N-acetylcolchinol using intramolecular biaryl oxidative coupling.

  2006cited by this paper
• Catalytic asymmetric vinylation and dienylation of ketones.

  2005cited by this paper
• Catalytic asymmetric addition of alkylzinc and functionalized alkylzinc reagents to ketones.

  2005cited by this paper
• Stereoselective generation of cis-2-lithio-3-CF3-oxirane via CF3-substituted β-oxido carbenoids. Highly stereoselective synthesis of CF3-substituted tri- and tetrasubstituted oxiranes and tetrasubstituted alkenes

  2003cited by this paper
• Enantioselective Synthesis by Lithiation Adjacent to Oxygen and Electrophile Incorporation

  2003cited by this paper
• Free-radical hydroxylation reactions of alkylboronates.

  2002cited by this paper
• New, General, and Stereoselective Synthesis of CF3-Containing Tri- and Tetrasubstituted Oxiranes and Tetrasubstituted Alkenes

  2001cited by this paper
• Asymmetric Hydrogenation of Alkenyl, Cyclopropyl, and Aryl Ketones. RuCl2(xylbinap)(1,2-diamine) as a Precatalyst Exhibiting a Wide Scope

  1998cited by this paper
• Unusual Regioselectivity in the Reaction of Allyl‐ or Allenylpropargyltitanium Compounds with Carbonyl Compounds: An Efficient Synthesis of Alkylidenecyclopropane Derivatives

  1996cited by this paper
• New, Efficient Method for the Synthesis of Allyltitanium Compounds from Allyl Halides or Allyl Alcohol Derivatives via Oxidative Addition. A Highly Efficient and Practical Synthesis of Homoallyl Alcohols

  1995cited by this paper
• Hindered organoboron groups in organic chemistry. 23. The interactions of dimesitylboron stabilised carbanions with aromatic ketones and aldehydes to give alkenes.

  1993cited by this paper
• Enantiomerically enriched 1-(N,N-diisopropylcarbamoyloxy)-1,3-dimethylallyllithium : stereochemistry of the stannylation, titanation, and the homoaldol reaction

  1992cited by this paper
• Direct insertion of alkali (alkaline earth) metals into allylic carbon-halogen bonds avoiding stereorandomization

  1991cited by this paper
• Oxiranyllithium reagents: Generation from organotin precursors, addition to aldehydes and ketones, and dimerization to α,α′-dialkoxyolefins

  1991cited by this paper
• Chiral Lithium‐1‐oxyalkanides by Asymmetric Deprotonation; Enantioselective Synthesis of 2‐Hydroxyalkanoic Acids and Secondary Alkanols

  1990cited by this paper
• Preparation of an Enantiomerically Enriched Allyllithium Derivative by Deprotonation with Kinetic Resolution of Enantiomers

  1990cited by this paper
• Metallated 2-alkenyl carbamates: chiral homoenolate reagents for asymmetric synthesis

  1990cited by this paper
• Biosynthesis of non-head-to-tail terpenes. Formation of 1'-1 and 1'-3 linkages

  1990cited by this paper
• Asymmetric Homoaldol Reaction by Enantioselective Lithiation of a Prochiral 2‐Butenyl Carbamate

  1989cited by this paper
• Synthesis of Alkyl-halides Under Neutral Conditions

  1989cited by this paper
• The total synthesis of 10-(R,S)-C30 botryococcene and botryococcane and a new synthesis of a general intermediate to the botryococcene family

  1989cited by this paper
• Enantiomerically enriched allystannanes from chiral allyllithium derivatives and their highly regio-, diastereo- and enantioselective hydroxyalkylation

  1989cited by this paper
• Organosilicon compounds with functional groups proximate to silicon: XVII. Synthetic and mechanistic aspects of the lithiation of α,β-epoxyalkylsilanes and related α-heterosubstituted epoxides

  1988cited by this paper
• α-Deprotonation of an α-Chiral 2-Alkenylcarbamate with Retention and Lithium-Titanium Exchange with Inversion— the Homoaldol Reaction with 1,3-Chirality Transfer†‡

  1986cited by this paper
• Organoboranes. 46. New procedures for the homologation of boronic esters. A critical examination of the available procedures to achieve convenient homologation of boronic esters

  1986cited by this paper
• Metallierte Stickstoff‐Derivate der Kohlensäure in der organischen Synthese, XXVII. – Homoaldol‐Reaktion, VII. Lithiierung acyclischer N, N‐Dialkylcarbamidsäure‐2‐alkenylester; Silylierung und γ‐selektive α‐Hydroxyalkylierung von Homoenolat‐Reagenzien

  1985cited by this paper
• The dimesitylboron group in organic synthesis 7. A unique variant of the Boron-Wittig reaction which stereoselectively yields 1,2-diols

  1985cited by this paper
• Structures of some botryococcenes: branched hydrocarbons from the b-race of the green alga Botryococcus braunii

  1985cited by this paper
• The Homoaldol Reaction, or How to Overcome Problems of Regio‐ and Stereo‐selectivity

  1984cited by this paper
• .alpha.-Trimethylsilyl boronic esters. Pinacol lithio(trimethylsilyl)methaneboronate, homologation of boronic esters with [chloro(trimethylsilyl)methyl]lithium, and comparisons with some phosphorus and sulfur analogs

  1983cited by this paper
• The dimesitylboron group in organic synthesis. 4. The ‘boron Wittig’ reaction

  1983cited by this paper
• .alpha.-Chloro boronic esters from homologation of boronic esters

  1980cited by this paper
• Synthesis of acyl halides under very mild conditions

  1980cited by this paper
• Studies directed toward the synthesis of prostaglandins. Useful boron-mediated olefin syntheses.

  1976cited by this paper
• Reaction of aldehydes and ketones with a boron-substituted carbanion, bis(ethylenedioxyboryl)methide. Simple aldehyde homologation

  1975cited by this paper
• Characterization of a boron-stabilized carbanion, tris(trimethylenedioxyboryl)methide ion, and its reactions with carbonyl compounds☆

  1975cited by this paper
• Alkene-1,1-diboronic esters from the condensation of triborylmethide anions with ketones or aldehydes☆

  1974cited by this paper
• Generation of boron-stabilized carbanions

  1972cited by this paper
• Alkene-1,1-diboronic esters from methanetetraboronic ester

  1970cited by this paper
• A convenient stereoselective synthesis of substituted alkenes via hydroboration-iodination of alkynes

  1967cited by this paper
• gem-Dimetallic compounds; A novel approach to olefins starting from carbonyl compounds and acetylenic derivatives.

  1966cited by this paper

• The epi-Matteson Reaction: Addition of Sodium Iodide in the Substitution Step Allows for a Stereodivergent Outcome.

  2025cites this paper
• Chemoselective and Stereoselective Allylation of Bis(alkenyl)boronates.

  2024cites this paper
• Recent advances in the chemistry of α-oxylboronate reagents

  2023cites this paper
• Pd-Catalyzed Organometallic-Free Homologation of Arylboronic Acids Enabled by Chemoselective Transmetalation

  2023cites this paper
• Lithiation–borylation methodology in the total synthesis of natural products

  2022cites this paper
• Stereodivergent Synthesis of 1,3-Dienes via Protodeboronation of Homoallenylboronic Esters.

  2022cites this paper
• Lithium

  2022cites this paper
• The Matteson Reaction

  2021cites this paper
• Three or Four Heteroatoms Including At Least One Boron

  2021cites this paper
• Sterically congested boronate and silane synthesis via electronically controlled protoboration and protosilylation

  2021cites this paper
• Studies on the Lithiation, Borylation, and 1,2‐Metalate Rearrangement of O‐Cycloalkyl 2,4,6‐Triisopropylbenzoates

  2021cites this paper
• Recent Advances of Applying Boron‐Reagents in Asymmetric Total Syntheses of Natural Products and Bio‐Active Molecules

  2020cites this paper
• Transition metal-free synthesis of alkyl pinacol boronates.

  2020cites this paper
• Nucleophilic Substitution at Quaternary Carbon Stereocenters.

  2020cites this paper
• Iterative Synthesis of Alkenes by Insertion of Lithiated Epoxides into Boronic Esters.

  2019cites this paper
• Recent advances in the borylative transformation of carbonyl and carboxyl compounds.

  2019cites this paper
• Guanidine-Copper Complex Catalyzed Allylic Borylation for the Enantioconvergent Synthesis of Tertiary Cyclic Allylboronates.

  2019cites this paper
• Vinylidene Homologation of Boronic Esters and its Application to the Synthesis of the Proposed Structure of Machillene.

  2019cites this paper
• Chemistry of the Secondary Metabolites of Termites.

  2019cites this paper
• 1,2‐Metallate Rearrangement of Boron Derivatives

  2019cites this paper
• Selective Synthesis of Botryococcene Pentaepoxide - The Chemical Modifications of the Algal Biomass Oil

  2018cites this paper
• The Molecular Industrial Revolution: Automated Synthesis of Small Molecules.

  2018cites this paper
• Kinetic Resolution of Secondary Allyl Boronates and Their Application in the Synthesis of Homoallylic Amines.

  2018cites this paper
• Total Synthesis of C30 Botryococcene and epi-Botryococcene by a Diastereoselective Ring Opening of Alkenylcyclopropanes.

  2018cites this paper
• Zirconocene-Mediated Selective C-C Bond Cleavage of Strained Carbocycles: Scope and Mechanism.

  2018cites this paper
• Heck Reaction of Electronically Diverse Tertiary Alkyl Halides.

  2018cites this paper
• Spectroscopic insight into supramolecular assemblies of boric acid derivatives and β-cyclodextrin.

  2018cites this paper
• Toward Generalization of Iterative Small Molecule Synthesis.

  2018cites this paper
• Site‐Selective Hydrosilylation of Botryococcene ‐ The Algal Biomass Hydrocarbon Oil

  2018cites this paper
• Die molekulare industrielle Revolution: zur automatisierten Synthese organischer Verbindungen

  2018cites this paper
• A Complementary Toolbox of Iterative Methods for the Stereoselective Synthesis of Heteroatom-Rich Motives from C1-Building Blocks

  2018cites this paper
• Transition-metal-free synthesis of 1,1-diboronate esters with a fully substituted benzylic center via diborylation of lithiated carbamates.

  2017cites this paper
• Enantiospecific Trifluoromethyl‐Radical‐Induced Three‐Component Coupling of Boronic Esters with Furans

  2017cites this paper
• Enantioselective Construction of Tertiary C-O Bond via Allylic Substitution of Vinylethylene Carbonates with Water and Alcohols.

  2017cites this paper
• Asymmetric Synthesis of Secondary and Tertiary Boronic Esters.

  2017cites this paper
• Asymmetrische Synthese sekundärer und tertiärer Boronsäureester

  2017cites this paper
• Merging allylic C–H bond activation and C–C bond cleavage en route to the formation of a quaternary carbon stereocenter in acyclic systems

  2016cites this paper
• High Precision Assembly Line Synthesis for Molecules with Tailored Shapes

  2016cites this paper
• Synthesis of 3-Aryl-1-aminopropane Derivatives: Lithiation–Borylation–Ring-Opening of Azetidinium Ions

  2016cites this paper
• Full chirality transfer in the synthesis of hindered tertiary boronic esters under in situ lithiation-borylation conditions.

  2016cites this paper
• Accessing Both Retention and Inversion Pathways in Stereospecific, Nickel-Catalyzed Miyaura Borylations of Allylic Pivalates.

  2016cites this paper
• Development of an Efficient Asymmetric Synthesis of the Chiral Quaternary 5-Lipoxygenase Activating Protein Inhibitor

  2016cites this paper
• Synthesis of Chiral Tertiary Boronic Esters by Oxime-Directed Catalytic Asymmetric Hydroboration.

  2016cites this paper
• l-Proline and thiourea co-catalyzed condensation of acetone

  2016cites this paper
• Design and Preparation of Polymer Resin‐Supported Proline Catalyst with Industrial Application Potential

  2016cites this paper
• Copper-catalyzed cross-coupling reactions of epoxides with gem-diborylmethane: access to γ-hydroxyl boronic esters.

  2016cites this paper
• Enantiospecific Alkynylation of Alkylboronic Esters

  2016cites this paper
• Short Convergent Synthesis of the Mycolactone Core Through Lithiation–Borylation Homologations

  2015cites this paper
• Generation, structure and reactivity of tertiary organolithium reagents.

  2015cites this paper
• Development of an asymmetric synthesis of a chiral quaternary FLAP inhibitor.

  2015cites this paper
• Regio- and Stereoselective Conjugate Addition of Aldehydes to β-Tosyl Enones under the Catalysis of a Binaphthyl-Modified Chiral Amine.

  2015cites this paper
• Design and application of the recyclable poly(L-proline-co-piperidine) catalyst for the synthesis of mesityl oxide from acetone

  2015cites this paper
• Reagent-controlled lithiation–borylation

  2015cites this paper
• Enantioselective synthesis of allylboronates and allylic alcohols by copper-catalyzed 1,6-boration.

  2014cites this paper
• Phosphine-catalyzed anti-carboboration of alkynoates with alkyl-, alkenyl-, and arylboranes.

  2014cites this paper
• A diastereoselective one-pot, three-step cascade toward α-substituted allylboronic esters.

  2014cites this paper
• 2.04 Heteroatom-Stabilized Allylic Anions

  2014cites this paper
• Lithium-Boron Chemistry: A Synergistic Strategy in Modern Synthesis

  2014cites this paper
• Catalytic Asymmetric Synthesis of Dihydrofurans and Cyclopentenols with Tertiary Stereocenters

  2014cites this paper
• Structure, Bonding, and Reactivity of Room-Temperature-Stable Lithium Chloride Carbenoids

  2014cites this paper
• Short stereoselective synthesis of the Phytophthora universal mating hormone α1 using lithiation/borylation reactions.

  2014cites this paper
• High Precision Assembly Line Synthesis for Molecules with Tailored Shapes

  2014cites this paper
• Lithiation-borylation methodology and its application in synthesis.

  2014cites this paper
• Synthetic Routes to Methylerythritol Phosphate Pathway Intermediates and Downstream Isoprenoids

  2014cites this paper
• Stereoselective allylboration of imines and indoles under mild conditions. An in situ E/Z isomerization of imines by allylboroxines

  2014cites this paper
• Highly selective allylborations of aldehydes using α,α-disubstituted allylic pinacol boronic esters.

  2014cites this paper
• Asymmetric substitution at the tetrasubstituted chiral carbon: catalytic ring-opening alkylation of racemic 2,2-disubstituted aziridines with 3-substituted oxindoles.

  2013cites this paper
• Selective formation of adjacent stereocenters by allylboration of ketones under mild neutral conditions.

  2013cites this paper
• Synthesis, reactions, applications, and biological activity of diethanolamine and its derivatives

  2013cites this paper
• Highly diastereo- and enantioselective allylboration of aldehydes using α-substituted allyl/crotyl pinacol boronic esters via in situ generated borinic esters.

  2013cites this paper
• Synthesis of enantioenriched tertiary boronic esters by the lithiation/borylation of secondary alkyl benzoates.

  2013cites this paper
• Migratory aptitudes of alkyl groups on boron: a computational study of halomethyllithium-induced migration reactions

  2013cites this paper
• Engineering triterpene metabolism in tobacco

  2012cites this paper
• Diastereodivergent synthesis of trisubstituted alkenes through protodeboronation of allylic boronic esters: application to the synthesis of the Californian red scale beetle pheromone.

  2012cites this paper
• Palladium-Catalyzed Synthesis and Isolation of Functionalized Allylboronic Acids: Selective, Direct Allylboration of Ketones

  2012cites this paper
• Enantioselective synthesis and cross-coupling of tertiary propargylic boronic esters using lithiation-borylation of propargylic carbamates.

  2012cites this paper
• Stereoselective preparation of β-aryl-β-boronyl enoates and their copper-catalyzed enantioselective conjugate reduction.

  2012cites this paper