SYNTHESIS OF ENANTIOPURE SYN-BETA-AMINO ALCOHOLS - A SIMPLE CASE OF CHELATION-CONTROLLED ADDITIONS OF DIETHYLZINC TO ALPHA-(DIBENZYLAMINO) ALDEHYDES

Authors
ANDRES JM BARRIO R MARTINEZ MA PEDROSA R PEREZENCABO A
Citation
Jm. Andres et al., SYNTHESIS OF ENANTIOPURE SYN-BETA-AMINO ALCOHOLS - A SIMPLE CASE OF CHELATION-CONTROLLED ADDITIONS OF DIETHYLZINC TO ALPHA-(DIBENZYLAMINO) ALDEHYDES, Journal of organic chemistry, 61(13), 1996, pp. 4210-4213
Citations number
29
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Journal of organic chemistry → ACNP
ISSN journal
00223263
Volume
61
Issue
13
Year of publication
1996
Pages
4210 - 4213
Database
ISI
SICI code
0022-3263(1996)61:13<4210:SOESA->2.0.ZU;2-D
Abstract
Enantiomerically pure syn-2-amino alcohols 6 are prepared by addition of diethylzinc to chiral alpha-(dibenzylamino) aldehydes 4. The additi on is highly stereoselective, leading to syn-2-(dibenzylamino) alcohol s 5 with excellent diastereomeric excesses (76-98%). Debenzylation of 5 by hydrogenolysis on Pearlman's catalyst yields quantitatively the a mino alcohols 6.