ASYMMETRIC CYCLIZATION VIA TANDEM CONJUGATE ADDITION BY USING METAL AMIDE REAGENTS - IMPORTANCE OF THE FOLDED ORIENTATION OF 2 ENOATE MOIETIES

被引：40

作者：

SHIDA, N ^{[1
]}

UYEHARA, T ^{[1
]}

YAMAMOTO, Y ^{[1
]}

机构：

[1] TOHOKU UNIV,FAC SCI,DEPT CHEM,SENDAI,MIYAGI 980,JAPAN

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1992年 / 57卷 / 19期

关键词：

D O I：

10.1021/jo00045a003

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Di-(-)-menthylnona-2,7-diene-1,9-dioate (1) is converted to (-)-menthyl 3(S)-(N-benzylamino)-2(S)-(-)-menthoxycarbonyl)-1(S)-cyclohexane-1-acetate (2) with high diastereoselectivity upon treatment with the amide cuprate or zincate reagent Bn(TMS)NML(n) in the presence of ZnCl2. The folded orientation of the two enoate moieties in 1 is essential for this high asymmetric cyclization via tandem conjugate addition.

引用

页码：5049 / 5051

页数：3

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