Short enantioselective syntheses of trans-5-alkylprolines from new functionalized amino alcohols.

No abstract is available for this paper.

• Publication year

  2008

• Venue

  Journal of Organic Chemistry

• Publication date

  2008-10-04

• Fields of study

  Medicine, Chemistry

• Identifiers
  DOI 10.1021/jo8014243PMID 18834177
• 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.

• Rational combination of two privileged chiral backbones: highly efficient organocatalysts for asymmetric direct aldol reactions between aromatic aldehydes and acylic ketones.

  2008cited by this paper
• Regiospecific organocatalytic asymmetric aldol reaction of methyl ketones and alpha,beta-unsaturated trifluoromethyl ketones.

  2007cited by this paper
• Highly enantioselective organocatalytic direct aldol reaction in an aqueous medium.

  2007cited by this paper
• A highly efficient asymmetric organocatalytic aldol reaction in a ball mill.

  2007cited by this paper
• Enantioselective organocatalytic aminomethylation of aldehydes: a role for ionic interactions and efficient access to beta2-amino acids.

  2006cited by this paper
• Chirospecific synthesis of spirocyclic beta-lactams and their characterization as potent type II beta-turn inducing peptide mimetics.

  2006cited by this paper
• Impact of Cis‐proline analogs on peptide conformation

  2006cited by this paper
• New synthesis of cis 5‐tert‐butyl‐L‐proline via cuprate. Evaluation as a cis proline mimetic in a biological active octapeptide

  2006cited by this paper
• An efficient, asymmetric organocatalyst-mediated conjugate addition of nitroalkanes to unsaturated cyclic and acyclic ketones.

  2006cited by this paper
• A highly efficient organocatalyst for direct aldol reactions of ketones with aldehydes [corrected].

  2005cited by this paper
• Novel approach to 5-substituted proline derivatives using a silver-catalyzed cyclization as the key step.

  2005cited by this paper
• In the golden age of organocatalysis.

  2004cited by this paper
• Enamine catalysis is a powerful strategy for the catalytic generation and use of carbanion equivalents.

  2004cited by this paper
• Conformationally rigid N-acyl-5-alkyl-L-prolyl-pyrrolidines as prolyl oligopeptidase inhibitors.

  2003cited by this paper
• Asymmetric synthesis of cis-5-tert-butylproline with metal carbenoid NH insertion.

  2003cited by this paper
• Asymmetric synthesis of substituted prolines from delta-amino beta-ketoesters. Methyl (2S,5R)-(+)-5-phenylpyrrolidine-2-carboxylate.

  2002cited by this paper
• Novel dipeptide macrocycles from 4-oxo, -thio, and -amino-substituted proline derivatives.

  2002cited by this paper
• Asymmetric syntheses of new functionalized beta-amino alcohols via diastereoselective addition of organometallic reagents onto oxazolidines.

  2002cited by this paper
• The intriguing reactivity of functionalized beta-amino alcohols with glyoxal: application to a new expedient enantioselective synthesis of trans-6-alkylpipecolic acids.

  2002cited by this paper
• Masked oxo sulfinimines (N-sulfinyl imines) in the asymmetric synthesis of proline and pipecolic acid derivatives.

  2001cited by this paper
• Design, synthesis, and conformational analysis of azacycloalkane amino acids as conformationally constrained probes for mimicry of peptide secondary structures.

  2001cited by this paper
• Conformationally constrained substance P analogues: the total synthesis of a constrained peptidomimetic for the Phe7-Phe8 region.

  2000cited by this paper
• Asymmetric Syntheses of 2-Substituted and 2,5-Disubstituted Pyrrolidines from (3S,5R,7aR)-5-(Benzotriazol-1-yl)-3-phenyl[2,1-b]oxazolopyrrolidine.

  1999cited by this paper
• Dopamine receptor modulation by a highly rigid spiro bicyclic peptidomimetic of Pro-Leu-Gly-NH2.

  1993cited by this paper
• Proline-dependent structural and biological properties of peptides and proteins.

  1993cited by this paper
• Proline residues in transmembrane helices: structural or dynamic role?

  1991cited by this paper

• Fused Nitrogen Bridgehead N,O‐Acetals as Versatile Scaffolds: Synthetic Strategies, Mechanism and Applications

  2025cites this paper
• Copper catalyzed Shono-type oxidation of proline residues in peptide

  2023cites this paper
• 3H-Pyrroles as a platform for the catalyst-free construction of dihydropyrrolo[2,1-b]oxazoles: [4 + 2]-cycloaddition vs [2 + 3]-annulation with 1-cyano-3-hydroxyalkynes

  2019cites this paper
• Enantiodivergent Synthesis of (+)- and (-)-Pyrrolidine 197B: Synthesis of trans-2,5-Disubstituted Pyrrolidines by Intramolecular Hydroamination.

  2016cites this paper
• Synthesis of enantiopure trans-2,5-disubstituted trifluoromethylpyrrolidines and (2S,5R)-5-trifluoromethylproline.

  2015cites this paper
• General Method of Synthesis for Naloxone, Naltrexone, Nalbuphone, and Nalbuphine by the Reaction of Grignard Reagents with an Oxazolidine Derived from Oxymorphone

  2013cites this paper
• From isoxazolidines to tetrahydro-1,3-oxazines for the synthesis of chiral pyrrolidines

  2012cites this paper
• Asymmetric synthesis of proline-based conformationally constrained tryptophan mimetic.

  2010cites this paper
• A versatile iron-catalyzed protocol for the one-pot synthesis of isoxazoles or isoxazolines from the same propargylic alcohols.

  2010cites this paper
• Synthesis of highly enantioenriched chiral alpha-aminoorganotins via diastereoselective ring opening of chiral N-(arenesulfonyl) 2-tributylstannyloxazolidines.

  2009cites this paper
• Palladium-catalyzed cyclization of unsaturated beta-amino alcohols: a new access to enantiopure bicyclic oxazolidines.

  2009cites this paper
• Short Enantioselective Syntheses of trans-5-Alkylprolines (IX) from New Functionalized Amino Alcohols (III).

  2009cites this paper