Mesyloxy-group migration as the stereoselective preparation method of various functionalized olefins and its reaction mechanism |
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Authors: | Yamazaki T Hiraoka S Sakamoto J Kitazume T |
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Institution: | Department of Bioengineering, Tokyo Institute of Technology, 4259 Nagatsuta-cho, Midori-ku, Yokohama 226-8501, Japan. tyamazak@bio.titech.ac.jp |
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Abstract: | structure: see text]. It was demonstrated that mesylation of appropriate gamma,gamma-difluorinated allylic alcohols under usual conditions furnished the corresponding alpha,alpha-difluorinated allylic mesylates, possibly by way of 1,3-mesyloxy-group migration after formation of the expected "normal" intermediates, gamma,gamma-difluorinated allylic mesylates. This rearrangement was conveniently applied to the construction of trisubstituted allylic alcohols, alpha,beta-unsaturated esters, amides, or ketones in good to excellent chemical yields with exclusive E selectivities. |
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