Preliminary studies on a novel synthesis of beta-amino acids: stereocontrolled transformation of D- and L-glyceraldehyde into 3-amino-2-(2 ',2 '-dimethyl-1 ',3 '-dioxolan-4 '-yl)propanoic acids

摘要

A stereocontrolled synthesis of the methyl ester of (2S)-3-amino-2-((4'S)-2',2'-dimethyl-1',3'-dioxolan-4'-yl)propanoic acid from D-glyceraldehyde is described for the first time. This method involves the stereoselective Michael addition of the lithium salt of tris(phenylthio)methane to (S)-2,2-dimethyl-4-((E)-2-nitrovinyl)-1,3-dioxolane followed by hydrolysis of the resulting (4S)-2,2dimethyl-4-((2'S)-3'-nitro-1',1',1'-tris(phenylthio)propan-2'-yl)-1,3-dioxolane to (2S)-methyl 2-((4'S)-2',2'-dimethyl-1',3'-dioxolan-4'-yl)-3-nitropropanoate which was finally reduced to the target compound. A similarly stereocontrolled transformation of L-glyceraldehyde into (2R)-methyl 3-amino-2-((4'R)-2',2'-dimethyl-1',3'-dioxolan-4'-yl)propanoate is also described. (c) 2006 Elsevier Ltd. All rights reserved.