对映体纯的顺式-β-氨基醇的合成。二乙基锌对α-（二苄基氨基）醛的螯合控制加成的一个简单实例。

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

作者信息

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

机构信息

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

出版信息

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

DOI:10.1021/jo960017t

PMID:11667317

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.

摘要

通过将二乙基锌加成到手性α-(二苄基氨基)醛4来制备对映体纯的顺式-2-氨基醇6。该加成反应具有高度的立体选择性，生成具有优异非对映体过量（76-98%）的顺式-2-(二苄基氨基)醇5。在Pearlman催化剂上通过氢解使5脱苄基定量地得到氨基醇6。