Direct catalytic asymmetric synthesis of cyclic aminals from aldehydes

Xu Cheng; Sreekumar Vellalath; Richard Goddard; Benjamin List

doi:10.1021/ja8071034

Direct catalytic asymmetric synthesis of cyclic aminals from aldehydes

J Am Chem Soc. 2008 Nov 26;130(47):15786-7. doi: 10.1021/ja8071034.

Authors

Xu Cheng¹, Sreekumar Vellalath, Richard Goddard, Benjamin List

Affiliation

¹ Max-Planck-Institut für Kohlenforschung, Kaiser-Wilhelm-Platz 1,D-45470, Mülheim an der Ruhr, Germany.

PMID: 18975905
DOI: 10.1021/ja8071034

Abstract

A highly enantioselective Brønsted acid catalyzed direct synthesis of cyclic aminals from aldehydes has been developed. The methodology has been applied to the first asymmetric synthesis of several antihypertensive aminal drugs including (R)-Thiabutazide.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Aldehydes / chemistry*
Amines / chemical synthesis*
Amines / chemistry
Catalysis
Chromatography, High Pressure Liquid
Cyclization
Models, Molecular
Molecular Structure
Stereoisomerism
ortho-Aminobenzoates / chemistry

Substances

Aldehydes
Amines
ortho-Aminobenzoates
anthranilamide