Catalytic asymmetric phase-transfer Michael reaction and Mannich-type reaction of glycine Schiff bases with tartrate-derived diammonium salts

被引：74

作者：

Shibuguchi, Tomoyuki ^{[1
]}

Mihara, Hisashi ^{[1
]}

Kuramochi, Akiyoshi ^{[1
]}

Ohshima, Takashi ^{[1
]}

Shibasaki, Masakatsu ^{[1
]}

机构：

[1] Univ Tokyo, Grad Sch Pharmaceut Sci, Bunkyo Ku, Tokyo 1130033, Japan

来源：

CHEMISTRY-AN ASIAN JOURNAL | 2007年 / 2卷 / 06期

关键词：

amino acids; asymmetric catalysis; conformation analysis; phase-transfer catalysis; Schiff bases;

D O I：

10.1002/asia.200700070

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Catalytic asymmetric Michael and Mannich-type reactions of glycine Schiff bases with chiral two-center organocatalysts, tartrate-derived diammonium salts (TaDiASs), are described. On the basis of conformational studies, optimized TaDiASs with a 2,6-disubstituted cyclohexane spiroacetal were newly designed. These TaDiASs catalyzed the asymmetric Michael and Mannich-type reactions of glycine Schiff bases with higher enantioselectivity than previous catalysts. In the Mannich-type reaction, aromatic N-Boc-protected imines (Boc=tert-butoxycarbonyl) as well as enolizable alkyl imines were applicable. As a synthetic application of the catalytic asymmetric Mannich-type reaction with the optimized TaDiASs, we developed a catalytic asymmetric total synthesis of (+)-nemonapride, which is an antipsychotic agent.

引用

页码：794 / 801

页数：8

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