Enantioselective reactions of tert-butyl glycinate-benzophenone Schiff base catalyzed by chiral phase-transfer catalyst in aqueous media without any organic solvent

被引：12

作者：

Mase, N ^{[1
]}

Ohno, T ^{[1
]}

Morimoto, H ^{[1
]}

Nitta, F ^{[1
]}

Yoda, H ^{[1
]}

Takabe, K ^{[1
]}

机构：

[1] Shizuoka Univ, Fac Engn, Dept Mol Sci, Hamamatsu, Shizuoka 4328561, Japan

来源：

TETRAHEDRON LETTERS | 2005年 / 46卷 / 18期

基金：

日本学术振兴会;

关键词：

chiral phase-transfer catalyst; asymmetric synthesis; aqueous media;

D O I：

10.1016/j.tetlet.2005.03.045

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Chiral phase-transfer catalyzed enantioselective alkylations of tert-butyl glycinate-benzophenone Schiff base were investigated in aqueous media without any organic solvent. Reactions in aqueous media smoothly proceeded to give the desired product in higher yield than under standard liquid-liquid biphasic conditions. In aqueous media the formation of benzophenone, which was caused by in situ hydrolysis of Schiff base, was depressed. (c) 2005 Elsevier Ltd. All rights reserved.

引用

页码：3213 / 3216

页数：4

共 3 条

[1] C2-symmetric chiral pentacyclic guanidine:: A phase-transfer catalyst for the asymmetric alkylation of tert-butyl glycinate Schiff base
Kita, T
Georgieva, A
Hashimoto, Y
Nakata, T
Nagasawa, K
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2002, 41 (15) : 2832 - +
[2] Palladium-catalyzed allylic alkylation of tert-butyl(diphylmethylene)-glycinate with simple allyl esters under chiral phase transfer conditions
Chen, GS
Deng, YJ
Gong, LZ
Mi, AQ
Cui, X
Jiang, YZ
Choi, MCK
Chan, ASC
TETRAHEDRON-ASYMMETRY, 2001, 12 (11) : 1567 - 1571
[3] Synthesis of chiral malonates by a-alkylation of 2,2-diphenylethyl tert-butyl malonates via enantioselective phase-transfer catalysis
Guo, Zhibin
Oh, Daehyun
Sagong, Min
Yang, Jewon
Lee, Geumwoo
Park, Hyeung-geun
FRONTIERS IN CHEMISTRY, 2023, 11

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