Diastereoselective Dimerisation of Alkenylthiazolines: A Combined Synthetic and Computational Study | Zendy

Beutler Ariane | Zendy; Davies Christopher D. | Zendy; Elliott Mark C. | Zendy; Galea Natasha M. | Zendy; Long Matthew S. | Zendy; Willock David J. | Zendy; Wood John L. | Zendy

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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)

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