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A Practical One-Pot Synthesis of Vinylstannanes from Ketones

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Alla Darwish and J. Michael Chong*

Guelph-Waterloo Centre for Graduate Work in Chemistry and Biochemistry (GWC), Department of Chemistry, University of Waterloo, Waterloo, Ontario, Canada N2L 3G1 jmchong@uwaterloo.ca

J. Org. Chem., 2007, 72 (4), pp 1507–1509

DOI: 10.1021/jo062145f

Publication Date (Web): January 25, 2007

In papers with more than one author, the asterisk indicates the name of the author to whom inquiries about the paper should be addressed.

Abstract

Treatment of ketones with Bu₃SnLi followed by addition of MsCl/Et₃N to the resulting alkoxide provides vinylstannanes. Cyclic vinylstannanes are particularly amenable to this procedure and isolated yields of 81−83% could be consistently attained. Traces of Bu₃SnH in crude reaction products could be removed by stirring in CHCl₃ with a catalytic amount of AIBN followed by filtration through silica gel.

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Published In Issue February 16, 2007
Received October 16, 2006

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A Practical One-Pot Synthesis of Vinylstannanes from Ketones

Abstract

Tools

SciFinder Links

History

Recommend & Share

Related Content

A Rapid, Asymmetric Synthesis of the Decahydrofluorene Core of the Hirsutellones

Synthesis of Isohasubanan Alkaloids via Enantioselective Ketone Allylation and Discovery of an Unexpected Rearrangement

Total Synthesis of Brevetoxin A

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