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Synthesis of 1,3-thiazolidines from aromatic thioketones and N-benzylidene α-amino acid esters via 1,3-dipolar cycloaddition of azomethine ylides


Gebert, Andreas; Linden, Anthony; Heimgartner, Heinz (2001). Synthesis of 1,3-thiazolidines from aromatic thioketones and N-benzylidene α-amino acid esters via 1,3-dipolar cycloaddition of azomethine ylides. Heterocycles, 54(2):691-704.

Abstract

The reaction of N-benzylidenephenylglycine methyl ester (2a) and N-benzylidenalanine methyl ester (2b) with thiobenzophenone (5a) and fluorene-9-thione (5b) in acetonitrile in the presence of lithium bromide and DBU gave a mixture of two corresponding diastereoisomeric [2+3] cycloadducts of types (6) and (7). The products were formed regioselectively and in good yields from the in situ generated metallo-azomethine ylides (8). The relative configurations of the two products (6c) and (7c) formed from fluorene-9-thione (5b) and 2a were established by X-Ray crystallography.

Abstract

The reaction of N-benzylidenephenylglycine methyl ester (2a) and N-benzylidenalanine methyl ester (2b) with thiobenzophenone (5a) and fluorene-9-thione (5b) in acetonitrile in the presence of lithium bromide and DBU gave a mixture of two corresponding diastereoisomeric [2+3] cycloadducts of types (6) and (7). The products were formed regioselectively and in good yields from the in situ generated metallo-azomethine ylides (8). The relative configurations of the two products (6c) and (7c) formed from fluorene-9-thione (5b) and 2a were established by X-Ray crystallography.

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Additional indexing

Item Type:Journal Article, refereed, original work
Communities & Collections:07 Faculty of Science > Department of Chemistry
Dewey Decimal Classification:540 Chemistry
Language:English
Date:2001
Deposited On:03 Oct 2013 08:40
Last Modified:05 Apr 2016 17:00
Publisher:The Japan Institute of Heterocyclic Chemistry
ISSN:0385-5414
Funders:Swiss National Science Foundation, F. Hoffmann-La Roche AG, Basel
Publisher DOI:https://doi.org/10.3987/COM-00-S(I)47

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