Asymmetric syntheses of 2-substituted and 2,5-disubstituted pyrrolidines from (3S,5R,7aR)-5-(benzotriazol-1-yl)-3-phenyl[2,1,b]oxazolopyrrolidine

被引：84

作者：

Katritzky, AR ^{[1
]}

Cui, XL

Yang, BZ

Steel, PJ

机构：

[1] Univ Florida, Dept Chem, Ctr Heterocycl Cpds, Gainesville, FL 32611 USA

[2] Univ Canterbury, Dept Chem, Christchurch 1, New Zealand

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1999年 / 64卷 / 06期

关键词：

D O I：

10.1021/jo9821426

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Benzotriazole, 2,5-dimethoxytetrahydrofuran, and (S)-phenylglycinol in one step gave 80% of (3S, 5R,7aR)-5-(benzotriazol-1-yl)-3-phenyl-[2,1-b]oxazolopyrrolidine (6), whose crystal structure was confirmed by X-ray crystallography. Novel chiral pyrrolidine synthon 6 reacts with organosilicon (allyltrimethylsilanes and vinyloxytrimethylsilanes), organophosphorus, organozinc, and Grignard reagents to afford chiral 2-substituted and 2,5-disubstituted pyrrolidines.

引用

页码：1979 / 1985

页数：7

共 63 条

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