SYNTHESIS OF OPTICALLY-ACTIVE BICYCLO[2.2.2]OCTANES - SUBSTITUTION EFFECT OF THE CYCLOHEXENONE RING ON THE SEQUENTIAL MICHAEL REACTION

被引：23

作者：

NAGAOKA, H ^{[1
]}

SHIBUYA, K ^{[1
]}

KOBAYASHI, K ^{[1
]}

MIURA, I ^{[1
]}

MURAMATSU, M ^{[1
]}

YAMADA, Y ^{[1
]}

机构：

[1] KOWA CO LTD,TOKYO RES LABS,TOKYO 189,JAPAN

来源：

TETRAHEDRON LETTERS | 1993年 / 34卷 / 25期

关键词：

D O I：

10.1016/S0040-4039(00)60610-X

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Reactions of the cross-conjugated dienolate of 3-substituted 2-cyclohexenone 1b and 1c, 2-cyclohexenone (1d), and 2,3-disubstituted 2-cyclohexenone le with methyl (S)-3-(2,2-dimethyl-1,3-dioxolan-4-yl)-2-propenate (Z)-2 gave highly diastereoselectively 3b, 3c, 3d and 3e, respectively. The presence of a methyl group at C-6 on cyclohexenone ring caused the stereoselectivity to change completely, so that the reaction of the lithium enolate of 9 with (Z)-2 and with (E)-2 gave predominantly 11 and 12, respectively.

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页码：4039 / 4042

页数：4

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