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Synlett 1995; 1995(6): 653-654
DOI: 10.1055/s-1995-5038
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Stereoselective Construction of Functionalized Cyclopropane Ring through [2+1] Type Condensation of α,β-Enones and Chiral Aldehydes

Tadashi Sato* , Satoshi Nagatsuka
  • *Department of Applied Chemistry, Waseda University, Ookubo 3, Shinjuku-ku, Tokyo 169, Japan, Fax 03-3209-3692
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Publication Date:
31 December 2000 (online)

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Enolates obtained by the 1,4-addition of Me3SnLi to α,β-enones react with aldehydes or ketones to afford β-stannyl-β’-hydroxy ketones. Treatment of the products with methanesulfonyl chloride or other suitable reagents affords acyl cyclopropane derivatives. Complete chiral transfer from chiral aldehydes to cyclopropane ring was achieved.

Chiral cyclopropane - cyclopropanation - organotin - β-stannyl-β’-hydroxy ketones