Literature DB >> 11667317

Synthesis of Enantiopure syn-beta-Amino Alcohols. A Simple Case of Chelation-Controlled Additions of Diethylzinc to alpha-(Dibenzylamino) Aldehydes.

José M. Andrés1, Roberto Barrio, María A. Martínez, Rafael Pedrosa, Alfonso Pérez-Encabo.   

Abstract

Enantiomerically pure syn-2-amino alcohols 6 are prepared by addition of diethylzinc to chiral alpha-(dibenzylamino) aldehydes 4. The addition is highly stereoselective, leading to syn-2-(dibenzylamino) alcohols 5 with excellent diastereomeric excesses (76-98%). Debenzylation of 5 by hydrogenolysis on Pearlman's catalyst yields quantitatively the amino alcohols 6.

Entities:  

Year:  1996        PMID： 11667317     DOI： 10.1021/jo960017t

Source DB:  PubMed          Journal:  J Org Chem        ISSN： 0022-3263            Impact factor:   4.354


  2 in total

1.  A general and simple diastereoselective reduction by L-Selectride: efficient synthesis of protected (4S,5S)-dihydroxy amides.

Authors:  Bo Yin; Dong-Nai Ye; Kai-Hui Yu; Liang-Xian Liu
Journal:  Molecules       Date:  2010-04-16       Impact factor: 4.411

2.  Limitations of Trifluoromethylbenzoimidazolylbenzoic Acid as a Chiral Derivatizing Agent to Assign Absolute Configuration for β-Chiral Aminoalcohols.

Authors:  Michal Kriegelstein; David Profous; Adam Přibylka; Antonín Lyčka; Petr Cankař
Journal:  ACS Omega       Date:  2022-04-04
  2 in total

北京卡尤迪生物科技股份有限公司 © 2022-2023.