Axially chiral analogues of 4-(dimethylamino)pyridine: Novel catalysts fornonenzymatic enantioselective acylations

Authors
Spivey, AC Fekner, T Spey, SE
Citation
Ac. Spivey et al., Axially chiral analogues of 4-(dimethylamino)pyridine: Novel catalysts fornonenzymatic enantioselective acylations, J ORG CHEM, 65(10), 2000, pp. 3154-3159
Citations number
47
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
JOURNAL OF ORGANIC CHEMISTRY
ISSN journal
00223263 → ACNP
Volume
65
Issue
10
Year of publication
2000
Pages
3154 - 3159
Database
ISI
SICI code
0022-3263(20000519)65:10<3154:ACAO4N>2.0.ZU;2-K
Abstract
A concise seven-step synthesis of atropisomeric S-aryl analogues of DMAP fr om 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 effi cient nucleophilic catalyst for kinetic resolution of a series of secondary alcohols on both an analytical and preparative scale (stereoselectivity fa ctors, s = 8.9-29).