Tetrahedron

N-bis-silylation of α-amino acids:“benzostabases” as amino protecting group

F Cavelier-Frontin, R Jacquier, J Paladino, J Verducci

Index: Cavelier-Frontin, Florine; Jacquier, Robert; Paladino, Joseph; Verducci, Jean Tetrahedron, 1991 , vol. 47, # 47 p. 9807 - 9822

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Citation Number: 17

Abstract

N-Bis-trimethylsilylation of α-amino acids using the powerful trimethylsilyl triflate reagent is difficult, and is rendered impossible in the case of bulky side-chains (valine). However, favorable entropy changes resulting from a cyclization reaction allow the formation of “benzostabase” N-diprotections regardless of the side-chain bulk.