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The influence of reaction conditions on the Diels–Alder cycloadditions of 2-thio-3-chloroacrylamides; investigation of thermal, catalytic and microwave conditions
Department of Chemistry, Analytical and Biological Chemistry Research Facility, University College Cork, Ireland
b
Department of Chemistry and School of Pharmacy, Analytical and Biological Chemistry Research Facility, University College Cork, Ireland
E-mail: a.maguire@ucc.ie
Org. Biomol. Chem., 2010,8, 5602-5613
DOI:
10.1039/C0OB00368A
Received
01 Jul 2010,
Accepted
31 Aug 2010
First published online
07 Oct 2010
The Diels–Alder cycloadditions of cyclopentadiene and 2,3-dimethyl-1,3-butadiene to a range of 2-thio-3-chloroacrylamides under thermal, catalytic and microwave conditions is described. The influence of reaction conditions on the outcome of the cycloadditions, in particular the stereoselectivity and reaction efficiency, is discussed. While the cycloadditions have been attempted at the sulfide, sulfoxide and sulfone levels of oxidation, use of the sulfoxide derivatives is clearly beneficial for stereoselective construction of Diels–Alder cycloadducts.
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Organic & Biomolecular Chemistry
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