[3,3]Sigmatropic ring expansion of cyclic thionocarbonates. 8. highly stereoselective synthesis of (Z- or (E)-double bonds by controlling chairlike-boatlike transition states in the [3,3]sigmatropic rearrangement of 8-membered thionocarbonates
作者： Shinya Harusawa , Hirotaka Osaki , Harumi Fujii , Ryuji Yoneda , Takushi Kurihara
DOI: 10.1016/S0040-4020(01)88312-5
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摘要: Abstract 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 [3,3]sigmatropic rearrangement 8-membered thionocarbonates (2). The geometry product appeared to be dependent on substituent pattern allylic system substrates (1). were readily converted (E)-allylic (11). Treatment (Z)-3j 3i with lithium liquid ammonia afforded (Z)-trisubstituted tetrasubstituted olefins (12j and 12i) high yields.
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