Chemical and Pharmaceutical Bulletin p. 1659 - 1667 (1991)
Update date:2022-08-05
Topics:
Harusawa
Osaki
Kurokawa
Fujii
Yoneda
Kurihara
Medium- and large-membered cyclic thiolcarbonates containing an (E)- or (Z)-double bond were synthesized by two methods using [3,3]sigmatropic ring expansion of cyclic thionocarbonates. The [3,3]sigmatropic ring expansion proceeds exclusively via the transition state bearing the chain tethered in a cis relationship when the cyclic thionocarbonates are 8-membered or smaller. Importantly, the ring of the cyclic thionocarbonates determines the double bond geometry of the thiolcarbonate. Conversion of the cyclic thiolcarbonates into (E)- or (Z)-allylic sulfides is also described.
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Doi:10.1016/S0040-4039(00)79406-8
(1991)Doi:10.1021/jo202688x
(2012)Doi:10.1016/0040-4039(91)80626-H
(1991)Doi:10.1080/00397919108021070
(1991)Doi:10.1248/cpb.39.1707
(1991)Doi:10.1016/S0040-4039(00)82184-X
(1988)
