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Trialkylsilyl Triflates-Practical Diastereoselective Catalysts in Conjugate Addition Reaction of Silyl Ketene Acetals and alfa, beta-Unsaturated Ketones

Michalak K., Wicha J.

Polish Journal of Chemistry

2004

Vol. 78 / nr 2

205-215

Catalytic effect of trimethylsilyl triflate (TMSOTf) or tert-butyldimethylsilyl triflate (TBSOTf) in conjugate addition reaction of the respective trialkylsilyl derivatives of thioester enolates (silyl ketene acetals) 2a-2e and _,_-unsaturated ketones 1a-1c has been studied. It was shown that silyl triflates are efficient catalysts with stereochemical profile similar to that of trityl hexachloroantimonate. The use of silyl triflates is particularly advantageous in tandem reactions involving conjugate addition as the first step.