Tetrahedron p. 6771 - 6790 (1989)
Update date:2022-08-04
Topics:
Barnish, Ian T.
Fishwick, Colin W. G.
Hill, David R.
Szantay, Csaba
A method has been developed for the efficient generation of 2-(N-acylamino)-1-thia-1,3-dienes.These novel hetero-dienes, which are generated via acylation of the corresponding thioamides, undergo irreversible regio- and stereospecific Diels-Alder addition to the starting thioamides to yield 6-(N-acylamino)-3,4-dihydro-2H-thiopyrans.The regiochemistry, relative configurations and the major solution conformations of the thiopyrans 4a-c and 10 have been determined using NMR techniques.In addition, it has been found that these systems exhibit a number of unique physical and chemical properties.
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