Tetrahedron

Generation and cycloadditions of 2-(N-acylamino)-1-thia-1, 3-dienes. Structural investigations using NMR methods. Part I.

IT Barnish, CWG Fishwick, DR Hill, C Szantay

Index: Barnish, Ian T.; Fishwick, Colin W. G.; Hill, David R.; Szantay, Csaba Tetrahedron, 1989 , vol. 45, # 21 p. 6771 - 6790

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Citation Number: 13

Abstract

A method has been developed for the efficient generation of2-(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 ...