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

José M. Andrés; Roberto Barrio; María A. Martínez; Rafael Pedrosa; Alfonso Pérez-Encabo

doi:10.1021/jo960017t

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

J Org Chem. 1996 Jun 26;61(13):4210-4213. doi: 10.1021/jo960017t.

Authors

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

Affiliation

¹ Departamento de Química Orgánica, Facultad de Ciencias, Universidad de Valladolid, Dr. Mergelina s/n, 47011-Valladolid, Spain.

PMID: 11667317
DOI: 10.1021/jo960017t

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.