One-Pot Synthesis of α-Amino Acids from Imines through CO2 Incorporation: An Alternative Method for Strecker Synthesis

被引：87

作者：

Mita, Tsuyoshi ^{[1
]}

Chen, Jianyang ^{[1
]}

Sugawara, Masumi ^{[1
]}

Sato, Yoshihiro ^{[1
]}

机构：

[1] Hokkaido Univ, Fac Pharmaceut Sci, Kita Ku, Nishi 6,Kita 12, Sapporo, Hokkaido 0600812, Japan

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2011年 / 50卷 / 06期

基金：

日本学术振兴会;

关键词：

amino acids; carbon dioxide fixation; imines; stannanes; umpolung; C-H BONDS; CATALYZED CARBOXYLATION; ORGANOMETALLIC REAGENTS; ORGANOZINC REAGENTS; CYCLIZATION; ESTERS; BETA;

D O I：

10.1002/anie.201006422

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Itas a gas: A novel one-pot process for the synthesis of α-amino acids from imine equivalents using CO2 gas as a carbon source has been developed. This reaction was made possible by the reagent combination of TMSSnBu3 and CsF (see scheme). Three successive reactions (imine formation, stannylation, and carboxylation) proceeded in the same flask under these conditions to give products in up to 79 % yield. Boc=tert-butoxycarbonyl, TMS=trimethylsilyl. © 2011 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

引用

页码：1393 / 1396

页数：4

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