Synthesis of 1-acylamino-1-(trimethylsiloxy) alkanes by trimethylsilyl trifluoromethanesulfonate-catalysed addition of bis (trimethylsilyl) amides to aldehydes

AP Johnson, RWA Luke, RW Steele…

Index: Johnson, A. Peter; Luke, Richard W. A.; Steele, Robert W.; Boa, Andrew N. Journal of the Chemical Society - Perkin Transactions 1, 1996 , # 9 p. 883 - 893

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Citation Number: 17

Abstract

Bis (trimethylsilyl) formamide reacts with aldehydes in refluxing chloroform, or at room temperature with catalysis by trimethylsilyl trifluoromethanesulfonate, to give 1-acylamino-1- (trimethylsiloxy) alkanes; similar results are obtained with other bis (trimethylsilyl) amides, but surprisingly not with bis (trimethylsilyl) acetamide, and addition of bis (trimethylsilyl) formamide to ketones and acetals can also be accomplished using TMS triflate as catalyst.