[1, 2] -Wittig Rearrangement Stereochemical Features and Synthetic Utilities

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概要

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• <I>The stereochemical features and synthetic potentials are described of the classic [1, 2] -Wittig rearrangement which is now recognized to proceed via the radical cleavagerecombination mechanism. First, the [1, 2] -Wittig rearrangement of enantio-defined α-benzyloxypropyllithium and its (R) -α-methylbenzyloxy analogs is shown to proceed predominantly with inversion of configuration at the Li-bearing terminus and retention of configuration at the migrating carbon. Second, the [1, 2] -Wittig rearrangement of O-glycosides of both acetal and ketal types, including those derived from D-ribose and D-glucose, is demonstrated to proceed with complete retention of either the α- or β-anomeric configuration, along with efficient stereocontrol over the newly created chiral center on the side chain to afford the novel classes of stereo-defined C-glycosides in good yields.</I>

• 社団法人 有機合成化学協会の論文

著者

• Tomooka Katsuhiko

  Department Of Chemistry Keio University

• Tomooka Katsuhiko

  Department Of Applied Chemistry Tokyo Institute Of Technology

• NAKAI Takeshi

  Department of Chemical Technology, Tokyo Institute of Technology

• Nakai Takeshi

  Department Of Applied Chemistry Tokyo Institute Of Technology

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