Organic Letters
Organic Letters
5 years ago

Synthesis of Methylenebicyclo[3.2.1]octanol by a Sm(II)-Induced 1,2-Rearrangement Reaction with Ring Expansion of Methylenebicyclo[4.2.0]octanone

Synthesis of Methylenebicyclo[3.2.1]octanol by a Sm(II)-Induced 1,2-Rearrangement Reaction with Ring Expansion of Methylenebicyclo[4.2.0]octanone
Hiroshi Kogen, Atsushi Kishida, Shinya Watanabe, Kazuma Matsunaga, Kokoro Nagasawa, Kazuhiko Takatori, Hiroto Nagaoka, Kenta Tendo, Shoya Ota
Direct conversion of methylenebicyclo[4.2.0]octanone to methylenebicyclo[3.2.1]octanol by a Sm(II)-induced 1,2-rearrangement with ring expansion of the methylenecyclobutane is described. Three conditions were optimized to allow the adaptation of this approach to various substrates. A rearrangement mechanism is proposed involving the generation of a ketyl radical and cyclopentanation by ketyl–olefin cyclization, followed by radical fragmentation and subsequent protonation.

Publisher URL: http://dx.doi.org/10.1021/acs.orglett.7b01604

DOI: 10.1021/acs.orglett.7b01604

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