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
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
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页码:1979 / 1985
页数:7
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