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Synlett 2001; 2001(2): 0214-0217
DOI: 10.1055/s-2001-10788
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Reductive Alkylation of γ-Cyano-α,β-unsaturated Ketones. A Modified Robinson Annulation Process to α,α-Disubstituted β,γ-unsaturated Cyclohexanone System

Chia-Liang Tai* , Tai Wei Ly, Jen-Dar Wu, Kak-Shan Shia, Hsiang-Jang Liu
  • *Department of Chemistry, National Tsing Hua University, Hsinchu, Taiwan 30013, R.O.C.; Fax +886-3-5720711; E-mail: hjliu§mx.nthu.edu.tw
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Publication Date:
31 December 2001 (online)

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Reductive alkylation of various 4-cyano-2-cyclohexenones, readily available from α-cyano ketones via a Robinson annulation process, gave rise to the corresponding 2,2-disubstituted-3-cyclohexenone derivatives in a completely regioselective manner. Application of this methodology resulted in an efficient synthesis of the marine natural product nanaimoal in racemic form.

ketones - cyano compounds - reduction - alkylation