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Organic letters

Practical synthesis of N-Boc- and N-Cbz-α-amido stannanes from α-amido sulfones using TMSSnBu3 and CsF.


PMID 21469722

Abstract

In the presence of TMSSnBu(3) and CsF, stannylation of N-Boc- and N-Cbz-α-amido sulfones proceeded very well to afford the corresponding α-amido stannanes in moderate-to-high yields. This reaction tolerated α-aryl-, alkenyl-, and alkyl-substituted α-amido sulfones as well as substrates containing either an ester or cyano moiety, which might be reactive with lithium or magnesium stannides employed in conventional stannylation.