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Memory of Chirality in the Electrochemical Oxidation of Thiazolidine-4-carboxylic Acid Derivatives


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Title: Memory of Chirality in the Electrochemical Oxidation of Thiazolidine-4-carboxylic Acid Derivatives
Authors: Onomura, Osamu / Ng’aNg’a Wanyoike, George / Matsumura, Yoshihiro / Kuriyama, Masami
Issue Date: 1-Mar-2010
Publisher: The Japan Institute of Heterocyclic Chemistry
Citation: HETEROCYCLES, 80(2), pp.1177-1185; 2010
Abstract: 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.
Keywords: Carbon-Carbon Bond Cleavage / Chiral N,O-Acetal / Electrochemical Oxidation / Memory of Chilarity / Thiazolidine-4-carboxylic Acid
URI: http://hdl.handle.net/10069/25429
ISSN: 03855414
DOI: 10.3987/COM-09-S(S)101
Rights: © 2010 The Japan Institute of Heterocyclic Chemistry Received.
Type: Journal Article
Text Version: author
Appears in Collections:Articles in academic journal

Citable URI : http://hdl.handle.net/10069/25429

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