A NOVEL BF(3)CENTER-DOT-OET(2)-CATALYZED [3+2] ANNULATION OF N-CBZ-ALPHA-AMINO ALDEHYDES WITH ALLYLTRIMETHYLSILANE - HIGHLY STEREOSELECTIVE SYNTHESIS OF CIS-2,3,5-TRISUBSTITUTED PYRROLIDINES

被引：46

作者：

KIYOOKA, S

SHIOMI, Y

KIRA, H

KANEKO, Y

TANIMORI, S

机构：

[1] Department of Chemistry, Kochi University, Kochi 780, Akebono-cho

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1994年 / 59卷 / 08期

关键词：

D O I：

10.1021/jo00087a003

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

In the presence of BF3.OEt(2) (0.2 molar equiv), the reactions (-10 degrees C, CH2Cl2) of N-Cbz-alpha-amino aldehydes with allyltrimethylsilane produced pyrrolidines in good yields (70-80%), with high all-cis stereoselectivity at the C12, C-3, and C-5 positions, along with small amounts of the expected homoallylic alcohols.

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页码：1958 / 1960

页数：3

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