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A short and general synthesis of α-ketoacylsilanes

✍ Scribed by Philip C.Bulman Page; Stephen Rosenthal

Book ID
104218657
Publisher
Elsevier Science
Year
1986
Tongue
French
Weight
110 KB
Volume
27
Category
Article
ISSN
0040-4039

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✦ Synopsis

a-Ketoacylsilanes may be prepared by the sequential osmium tetroxide catalysed dihydroxylation and Swern oxidation of cis-vinylsilanes.

Addition of nucleophiles to a-ketoacylsilanes occurs to give products arising exclusively from reactions at the silicon-bearing carbonyl group.

As a part of our continuing interest in acylsilane chemistry' we required a general preparative method for a-ketoacylsilanes (1). Reich* has reported the isolation of a-ketoacylsilane (2) by epoxidation and rearrangement of allene (3), however this procedure does not allow the preparation of a-ketoacylsilanes which do not possess a-hydrogen atoms.

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