Practical asymmetric synthesis of alpha-branched 2-piperazinylbenzylamines by 1,2-additions of organometallic reagents to N-tert-butanesulfinyl imines.

No abstract is available for this paper.

• Publication year

  2005

• Venue

  Journal of Organic Chemistry

• Publication date

  2005-09-24

• Fields of study

  Medicine, Chemistry

• Identifiers
  DOI 10.1021/JO051514PPMID 16238329
• 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.

• 3-[(2R)-Amino-2-phenylethyl]-1-(2,6-difluorobenzyl)-5-(2-fluoro-3-methoxyphenyl)- 6-methylpyrimidin-2,4-dione (NBI 42902) as a potent and orally active antagonist of the human gonadotropin-releasing hormone receptor. Design, synthesis, and in vitro and in vivo characterization.

  2005cited by this paper
• Stille coupling of stereochemically defined alpha-sulfonamidoorganostannanes.

  2004cited by this paper
• Very high 1,2- and 1,3-asymmetric induction in the reactions of allylic boron compounds with chiral imines.

  1986cited by this paper
• Reinvestigation of the chemistry of arylcarbenes in polycrystalline alcohols at 77K. Secondary photochemistry of matrix-isolated carbenes.

  1986cited by this paper

• Synthesis of Highly Functionalized Pyridines: A Metal-Free Cascade Process.

  2021cites this paper
• Addition of Non-Stabilized Carbon-Based Nucleophilic Reagents to ChiralN-Sulfinyl Imines

  2019cites this paper
• Next Generation of Fluorine-Containing Pharmaceuticals, Compounds Currently in Phase II-III Clinical Trials of Major Pharmaceutical Companies: New Structural Trends and Therapeutic Areas.

  2016cites this paper
• Ni-catalyzed asymmetric decarboxylative Mannich reaction for the synthesis of β-trifluoromethyl-β-amino ketones

  2015cites this paper
• Asymmetric Synthesis of Heterocyclic Analogues of a CGRP Receptor Antagonist for Treating Migraine.

  2015cites this paper
• General asymmetric synthesis of 2,2,2-trifluoro-1-(1H-indol-3- and -2-yl)ethanamines

  2015cites this paper
• Concise and scalable asymmetric synthesis of 5-(1-amino-2,2,2-trifluoroethyl)thiazolo[3,2-b][1,2,4]triazoles.

  2014cites this paper
• Mechanistic insights on the stereoselective nucleophilic 1,2-addition to sulfinyl imines.

  2014cites this paper
• SYNTHESIS OF DE NOVO CHIRAL γ-AMINO-YNAMIDES USING LITHIATED YNAMIDES. OBSERVATION OF A UNIQUE 5-ENDO-DIG CYCLIZATION WITH AN INVERSION OF S-CENTER.

  2014cites this paper
• Concise Asymmetric Synthesis of β‐Trifluoromethylated α,β‐Diamino Esters through Addition Reactions of Glycine Esters to CF3‐Sulfinylimine

  2014cites this paper
• Mannich‐Type Addition Reactions between Lithium Derivatives of Benzo[d]thiazoles and N‐tert‐Butylsulfinyl‐3,3,3‐trifluoroacetaldimine: Convenient Generalized Synthesis of Bis(benzothiazole)s

  2014cites this paper
• Asymmetric addition of aryloxy ethynyl lithium derivatives to N-sulfinyl imines

  2013cites this paper
• Intermolecular alkyl radical additions to enantiopure N-tert-butanesulfinyl aldimines.

  2013cites this paper
• A highly stereoselective addition of lithiated ynamides to Ellman-Davis chiral N-tert-butanesulfinyl imines.

  2013cites this paper
• Asymmetric addition of alkoxy ethynyl anion to chiral N-sulfinyl imines.

  2012cites this paper
• Asymmetric synthesis of β-aryl-β-trifluoromethyl-β-aminoarones via Mannich-type reactions of ketone enolates with chiral aryl CF3-substituted N-tert-butanesulfinyl ketimines

  2012cites this paper
• A facile process for the asymmetric synthesis of β-trifluoromethylated β-amino ketones via addition of ketone enolates to sulfinylimine.

  2011cites this paper
• Novel 7-phenylsulfanyl-1,2,3,4,10,10a-hexahydro-pyrazino[1,2-a]indoles as dual serotonin 5-HT2C and 5-HT6 receptor ligands.

  2010cites this paper
• Synthesis and applications of tert-butanesulfinamide.

  2010cites this paper
• Highly diastereoselective synthesis of α-trifluoromethylated α-propargylamines by acetylide addition to chiral CF3-substituted N-tert-butanesulfinyl ketimines

  2010cites this paper
• Efficient synthesis of a 7-azabicyclo[2.2.1]heptane based GlyT1 uptake inhibitor

  2010cites this paper
• Rhodium-catalyzed diastereoselective 1,2-addition of arylboronic acids to chiral trifluoroethyl imine

  2009cites this paper
• tert-Butanesulfinimines: structure, synthesis and synthetic applications.

  2009cites this paper
• Design and synthesis of 3-arylpyrrolidine-2-carboxamide derivatives as melanocortin-4 receptor ligands.

  2008cites this paper
• Syntheses of tetrahydrothiophenes and tetrahydrofurans and studies of their derivatives as melanocortin-4 receptor ligands.

  2008cites this paper
• Identification and characterization of pyrrolidine diastereoisomers as potent functional agonists and antagonists of the human melanocortin-4 receptor.

  2008cites this paper
• Pharmacological and pharmacokinetic characterization of 2-piperazine-alpha-isopropyl benzylamine derivatives as melanocortin-4 receptor antagonists.

  2008cites this paper
• Synthesis and characterization of pyrrolidine derivatives as potent agonists of the human melanocortin-4 receptor.

  2007cites this paper
• Design, synthesis, in vitro, and in vivo characterization of phenylpiperazines and pyridinylpiperazines as potent and selective antagonists of the melanocortin-4 receptor.

  2007cites this paper
• Highly diastereoselective reactions of 2-lithiated indoles with chiral N-tert-butanesulfinyl aldimines for the synthesis of chiral (2-indolyl) methanamine derivatives

  2007cites this paper
• Discovery of 1-[2-[(1S)-(3-dimethylaminopropionyl)amino-2-methylpropyl]-4-methylphenyl]-4-[(2R)-methyl-3-(4-chlorophenyl)-propionyl]piperazine as an orally active antagonist of the melanocortin-4 receptor for the potential treatment of cachexia.

  2007cites this paper
• Pyrrolidines as potent functional agonists of the human melanocortin-4 receptor.

  2007cites this paper
• Asymmetric syntheses of 1-aryl-2,2,2-trifluoroethylamines via diastereoselective 1,2-addition of arylmetals to 2-methyl-N-(2,2,2-trifluoroethylidene)propane-2-sulfinamide.

  2007cites this paper
• Pyrrolidinones as orally bioavailable antagonists of the human melanocortin-4 receptor with anti-cachectic activity.

  2007cites this paper
• Arylpropionylpiperazines as antagonists of the human melanocortin-4 receptor.

  2006cites this paper
• Propionylpiperazines as human melanocortin-4 receptor ligands.

  2006cites this paper