MEMORY OF CHIRALITY IN THE ELECTROCHEMICAL OXIDATION OF THIAZOLIDINE-4-CARBOXYLIC ACID DERIVATIVES

被引：13

作者：

Wanyoike, George Ng'aNg'a ^{[1
]}

Matsumura, Yoshihiro ^{[1
]}

Kuriyama, Masami ^{[1
]}

Onomura, Osamu ^{[1
]}

机构：

[1] Nagasaki Univ, Grad Sch Biomed Sci, Nagasaki 8528521, Japan

来源：

HETEROCYCLES | 2010年 / 80卷 / 02期

关键词：

Electrochemical Oxidation; Memory of Chilarity; Carbon-Carbon Bond Cleavage; Chiral N; O-Acetal; Thiazolidine-4-carboxylic Acid; ALPHA-AMINO-ACIDS; ASYMMETRIC CYCLIZATION; PRINCIPLE; CHEMISTRY;

D O I：

10.3987/COM-09-S(S)101

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Memory of chirality in the electrochemical oxidation of thiazolidine-4-carboxylic acid derivatives was observed. The relatively larger size of sulphur atom than the oxygen atom for oxazolidine-4-carboxylic acid derivative may slightly improved the enantioselectivities of the oxidized products. The bulkier penicillamine derivative 1c furnished 2c with much better enantioselectivity (91% ee) than that of the cysteine derivative 2b (85% ee). The presence of two extra dimethyl groups, for the penicillamine derivative improved the enantioselectivities of the thiazolidine derivatives from 85% ee to 91% ee.

引用

页码：1177 / 1185

页数：9

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