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Diastereoselective Dimerisation of Alkenylthiazolines: A Combined Synthetic and Computational Study
Author(s) -
Beutler Ariane,
Davies Christopher D.,
Elliott Mark C.,
Galea Natasha M.,
Long Matthew S.,
Willock David J.,
Wood John L.
Publication year - 2005
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.200500360
Subject(s) - chemistry , trifluoroacetic anhydride , trifluoroacetic acid , double bond , scope (computer science) , reaction mechanism , organic chemistry , chloride , computational chemistry , combinatorial chemistry , stereochemistry , medicinal chemistry , catalysis , computer science , programming language
The acylative dimerisation of 2‐alkenyl‐1,3‐thiazolines 1 gives compounds 3 and 8 upon treatment with trichloroacetyl chloride and trifluoroacetic anhydride, respectively. This reaction is completely diastereoselective, in particular giving only a single double‐bond isomer. The scope of the reaction has been evaluated synthetically, while a computational study has elucidated the mechanism of the reaction and the origin of stereocontrol. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2005)