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Synlett 1999; 1999(5): 644-646
DOI: 10.1055/s-1999-2686
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A Novel Method for the Stereoselective Formation of Trans Bicyclic Ketones by Way of Oxidative Radical Cyclization

Takashi Takahashi* , Satoshi Tomida, Takayuki Doi
  • *Department of Chemical Engineering, Tokyo Institute of Technology, 2-12-1 Ookayama, Meguro, Tokyo 152-8552, Japan; Fax +81-3-57 34-28 84; E-mail: ttakashi@o.cc.titech.ac.jp
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Publication Date:
31 December 1999 (online)

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The stereoselective formation of cyanohydrin 4 was achieved by radical cyclization-oxygen trapping reaction of 5 into an intramolecular acrylic nitrile moiety. The cyanohydrin was used for ring closure reaction with a tosylate, providing the bicyclic systems 1 and 2 with a trans ring fusion.

bicyclo[4.3.0]nonan-1-one - bicyclo[4.4.0]decan-1-one - oxidative radical cyclization - cyanohydrin - intramolecular alkylation

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