A halide-initiated aza-Baylis–Hillman reaction: generation of unnatural amino acids

LO Davis, SL Tobey

Index: Davis, Lindsey O.; Tobey, Suzanne L. Tetrahedron Letters, 2010 , vol. 51, # 47 p. 6078 - 6081

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Abstract

A series of allenic ketones react with a glyoxylate-derived imine in the presence of MgBr2 through an aza-Morita–Baylis–Hillman (MBH) reaction. The isolation of a variety of unnatural amino acids with unique allene-containing functional groups provides a conceptually new application of the aza-MBH. The reaction scope and preliminary mechanistic investigations are discussed.