Catalytic Enantioselective Protonation of α-Oxygenated Ester Enolates Prepared through Phospha-Brook Rearrangement

被引：120

作者：

Hayashi, Masashi ^{[1
]}

Nakamura, Shuichi ^{[1
]}

机构：

[1] Nagoya Inst Technol, Dept Frontier Mat, Grad Sch Engn, Showa Ku, Nagoya, Aichi 4668555, Japan

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2011年 / 50卷 / 10期

关键词：

enantioselectivity; enolates; organocatalysis; phospha-Brook rearrangement; protonation; ASYMMETRIC HYDROPHOSPHONYLATION; HYDROXY PHOSPHONATES; ACID; DERIVATIVES; KETONES; DECARBOXYLATION; ALDEHYDES; EFFICIENT; AMINO;

D O I：

10.1002/anie.201007568

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

(Chemical Equation Presented) Phosphonates go chiral: The organocatalytic enantioselective reaction of α-ketoesters with phosphites using cinchona alkaloids and Na2CO3 has afforded α-phosphonyloxy esters with high enantioselectivities (see scheme). This process allows the formation of both enantiomers of the product. A catalyst loading of as low as 2 mol% does not result in a significant decrease of the enantioselectivity. © 2011 Wiley-VCH Verlag GmbH & Co. KGaA.

引用

页码：2249 / 2252

页数：4

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