Highly Diastereoselective Additions to α-Silyloxy
Ketones

G. R. Stanton; G. Koz; P. J. Walsh

doi:10.1055/s-0030-1260722

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Synfacts 2011(8): 0883-0883
DOI: 10.1055/s-0030-1260722

Metal-Mediated Synthesis

Highly Diastereoselective Additions to α-Silyloxy Ketones

Contributor(s): Paul Knochel, Andreas J. Wagner
G. R. Stanton, G. Koz, P. J. Walsh*
University of Pennsylvania, Philadelphia, USA

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Publication History

Publication Date:
20 July 2011 (online)

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Significance

A highly diastereoselective and general method for the addition of variously substituted alkenylzinc reagents to α-silyloxy ketones is reported. An excess of alkylzinc halide as Lewis acid leads to the formation of chelation-controlled products in diastereomeric ratios greater than 18:1.