Tetrahedron p. 9433 - 9450 (1992)
Update date:2022-08-06
Topics: Stereoselective synthesis [3,3]Sigmatropic ring expansion Thionocarbonates (E)-double bonds (Z)-double bonds Chairlike-boatlike transition states 8-membered thionocarbonates
Harusawa
Osaki
Fujii
Yoneda
Kurihara
A highly stereoselective synthesis of (Z)- or (E)-double bonds in 10-membered thiolcarbonates (3) was successfully conducted by controlling the chairlike-boatlike transition states in the [3,3]sigmatropic rearrangement of 8-membered thionocarbonates (2). The geometry of the product appeared to be highly dependent on the substituent pattern in the allylic system of the substrates (1). The 10-membered thiolcarbonates (3) were readily converted to (Z)- or (E)-allylic thiolcarbonates (11). Treatment of (Z)-3j or 3i with lithium in liquid ammonia afforded (Z)-trisubstituted or tetrasubstituted olefins (12j and 12i) in high yields.
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Doi:10.1246/bcsj.65.1096
(1992)Doi:10.1039/c4cc01255k
(2014)Doi:10.1016/j.bmcl.2013.08.027
(2013)Doi:10.1055/s-1992-26327
(1992)Doi:10.1016/j.tetasy.2013.07.005
(2013)Doi:10.1126/science.115.2978.84-a
(1952)