Highly stereoselective reduction of acyclic α-sulfinyl ketimines: synthesis of enantiomerically pure β-aminosulfoxides

The DIBAL reduction of enantiomerically pure α-sulfinyl ketimines can be achieved almost completely stereoselectively under ZnX 2 catalysis, regardless of the alkyl or aryl substituent at nitrogen and the aliphatic (cyclic or acyclic) or aromatic character of the imine. Steric factors as well as the...

Full description

Saved in:
Bibliographic Details
Published in:Tetrahedron: asymmetry 1999-12, Vol.10 (23), p.4607-4618
Main Authors: Garcı́a Ruano, José L, Cifuentes, Marta M, Lorente, Antonio, Rodrı́guez Ramos, Jesús H
Format: Article
Language:English
Citations: Items that this one cites
Items that cite this one
Online Access:Get full text
Tags: Add Tag
No Tags, Be the first to tag this record!
Description
Summary:The DIBAL reduction of enantiomerically pure α-sulfinyl ketimines can be achieved almost completely stereoselectively under ZnX 2 catalysis, regardless of the alkyl or aryl substituent at nitrogen and the aliphatic (cyclic or acyclic) or aromatic character of the imine. Steric factors as well as the electrophilic character of the hydride are responsible for the stereochemical course of the reduction.
ISSN:0957-4166
1362-511X
DOI:10.1016/S0957-4166(99)00523-6