Axially Chiral Analogues of 4-(Dimethylamino)pyridine:  Novel Catalysts for Nonenzymatic Enantioselective Acylations

A concise seven-step synthesis of atropisomeric 3-aryl analogues of DMAP from 4-pyridone 8 has been developed. A representative compound of this class, biaryl (±)-15, has been resolved using CSP HPLC and shown to be an efficient nucleophilic catalyst for kinetic resolution of a series of secondary a...

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Bibliographic Details
Published in:Journal of organic chemistry 2000-05, Vol.65 (10), p.3154-3159
Main Authors: Spivey, Alan C, Fekner, Tomasz, Spey, Sharon E
Format: Article
Language:English
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Summary:A concise seven-step synthesis of atropisomeric 3-aryl analogues of DMAP from 4-pyridone 8 has been developed. A representative compound of this class, biaryl (±)-15, has been resolved using CSP HPLC and shown to be an efficient nucleophilic catalyst for kinetic resolution of a series of secondary alcohols on both an analytical and preparative scale (stereoselectivity factors, s = 8.9−29).
ISSN:0022-3263
1520-6904
DOI:10.1021/jo0000574