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Stereoselective 1,3-dipolar cycloaddition of an azomethine ylide with a chiral 1,3-thiazole-5(4H)-thione


Gebert, Andreas; Linden, Anthony; Mloston, Grzegorz; Heimgartner, Heinz (2002). Stereoselective 1,3-dipolar cycloaddition of an azomethine ylide with a chiral 1,3-thiazole-5(4H)-thione. Heterocycles, 56(1-2):393-402.

Abstract

The reaction of cis-1-methyl-2,3-diphenylaziridine (2) with racemic 4-benzyl-4-methyl-2-phenyl-1,3-thiazole-5(4H)-thione (rac-1b) in toluene at 100-105°C gave a single spirocyclic [2+3] cycloadduct (rac-5). Its structure and relative configuration was established by X-Ray crystallography. Starting with enantiomerically pure (R)-1b and (S)-1b, the enantiomers (4R,5R,7S,9R)-5 and (4S,5S,7R,9S)-5, respectively, were formed in a regio- and stereoselective 1,3-dipolar cycloaddition of the in situ generated (E,Z)-configured N-methyl-1,3-diphenylazomethine ylide (4).

The reaction of cis-1-methyl-2,3-diphenylaziridine (2) with racemic 4-benzyl-4-methyl-2-phenyl-1,3-thiazole-5(4H)-thione (rac-1b) in toluene at 100-105°C gave a single spirocyclic [2+3] cycloadduct (rac-5). Its structure and relative configuration was established by X-Ray crystallography. Starting with enantiomerically pure (R)-1b and (S)-1b, the enantiomers (4R,5R,7S,9R)-5 and (4S,5S,7R,9S)-5, respectively, were formed in a regio- and stereoselective 1,3-dipolar cycloaddition of the in situ generated (E,Z)-configured N-methyl-1,3-diphenylazomethine ylide (4).

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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:2002
Deposited On:03 Oct 2013 08:53
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-01-S(K)57
Permanent URL: https://doi.org/10.5167/uzh-81406

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