Practical modifications and applications of the sharpless asymmetric aminohydroxylation in the one-pot preparation of chiral oxazolidin-2-ones

被引：44

作者：

Barta, NS ^{[1
]}

Sidler, DR ^{[1
]}

Somerville, KB ^{[1
]}

Weissman, SA ^{[1
]}

Larsen, RD ^{[1
]}

Reider, PJ ^{[1
]}

机构：

[1] Merck & Co Inc, Merck Res Labs, Dept Proc Res, Rahway, NJ 07065 USA

来源：

ORGANIC LETTERS | 2000年 / 2卷 / 18期

关键词：

D O I：

10.1021/ol006255z

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Chiral oxazolidin-2-ones are synthetically valuable as chiral auxiliaries, and many have pharmaceutically interesting biological activity. This communication focuses on a convenient, practical one-pot preparation of chiral 4,5-disubstituted oxazolidan-2-ones in good yield with high enantioselectivities, using a modified Sharpless asymmetric aminohydroxylation of beta-substituted styrene derivatives followed by base-mediated ring closure. This procedure has been demonstrated on both small and large scale, utilizing 1,3 dichloro-5,5 dimethyl hydantoin as an easily handled, commercially available substitute for tert-butyl hypochlorite.

引用

页码：2821 / 2824

页数：4

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