[2,3]-Wittig sigmatropic rearrangement of crotyl propargyl ether system. An emerging tool for control of acyclic stereochemistry |
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Authors: | Kōichi Mikami Ken-Ichi Azuma Takeshi Nakai |
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Institution: | Department of Chemical Technology, Tokyo Institute of Technology, Meguro, Tokyo 152 Japan |
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Abstract: | The 2,3]-Wittig rearrangement of properly designated (E)- and (Z)-crotyl propargyl ether system has been shown to exhibit a remarkably high degree of threo- and erythro -selection, respectively, and the stereochemical outcomes are discussed on mechanistic grounds. Some useful transformations of the rearrangement product are also described within the context of the formal total synthesis of (±)-oudemansin. Further, the high level of diastereoselection is maintained in the reaction of the α-methylcrotyl counterparts, together with the exclusive formation of the (E)-olefinic bond. |
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