Axially Chiral Analogues of 4-(Dimethylamino)pyridine: Novel Catalysts for Nonenzymatic Enantioselective Acylations
- 18 April 2000
- journal article
- research article
- Published by American Chemical Society (ACS) in The Journal of Organic Chemistry
- Vol. 65 (10) , 3154-3159
- https://doi.org/10.1021/jo0000574
Abstract
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).Keywords
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