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Synlett 2005(17): 2643-2647
DOI: 10.1055/s-2005-917073
DOI: 10.1055/s-2005-917073
LETTER
© Georg Thieme Verlag Stuttgart · New York
1,4-Bis(arylsulfonyl)-1,2,3,4-tetrahydropyridines in Synthesis: Stereoselective Homo- and Hetero-Diels-Alder Reactions
Further Information
Received
21 July 2005
Publication Date:
05 October 2005 (online)
Publication History
Publication Date:
05 October 2005 (online)
Abstract
Palladium-catalysed coupling of a vinylstannane or vinyl boronic acids with 5-iodo-1,4-bis(tosyl)-1,2,3,4-tetrahydropyridines yields 1,3-dienes. These participate in homo- and hetero-Diels-Alder reactions with unsaturated carbonyl compounds and with nitroso species generated in situ to give novel bicyclic compounds in a highly stereoselective fashion.
Key words
Diels-Alder reaction - nitroso dienophile - palladium-catalysed coupling - stereoselective synthesis - tetrahydropyridine
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References
We thank Dr. A. J. P. White (Imperial College) for the X-ray structure determinations. Full details will be reported elsewhere.
12Nitrosobenzene was purchased from Aldrich Chemical Co. and used as supplied.