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(BDP)CuH: A “Hot” Stryker's Reagent for Use in Achiral Conjugate Reductions

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Benjamin A. Baker, Žarko V. Bošković, and Bruce H. Lipshutz*

Department of Chemistry and Biochemistry, University of California, Santa Barbara, California 93106

Org. Lett., 2008, 10 (2), pp 289–292

DOI: 10.1021/ol702689v

Publication Date (Web): December 20, 2007

Section:

General Organic Chemistry

Abstract

A ligand-modified, economical version of Stryker's reagent (SR) has been developed based on a bidentate, achiral bis-phosphine. Generated in situ, “(BDP)CuH” smoothly effects conjugate reductions of a variety of unsaturated substrates, including those that are normally unreactive toward SR. Substrate-to-ligand ratios typically on the order of 1000−10000:1 can be used leading to products in high yields.

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