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New C=C Bond Formation via Nonstoichiometric Titanium(IV) Halide Mediated Vicinal Difunctionalization of α,β-Unsaturated Acyclic Ketones

Guigen Li*, Joe Gao, Han-Xun Wei and Mason Enright

*Department of Chemistry and Biochemistry, Texas Tech University, Lubbock, Texas 79409-1061, Email: guigen.littu.edu

G. Li, J. Gao, H.-X. Wei, M. Enright, Org. Lett., 2000, 2, 617-620.

DOI: 10.1021/ol9904040 (free Supporting Information)


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Abstract

Titanium(IV) halides mediate a highly stereoselective vicinal difuctionalization of α,β-unsaturated ketones to provide multifunctionalized trisubstituted alkenes in very good yields and high Z:E stereoselectivity. The reaction can be performed at room temperature in a convenient vial under air.

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Key Words

enones, allyl chlorides


ID: J54-Y2000