Synthesis of Stereospecific Deuterium-Labeled Homoserines and Homoserine Lactones

Article abstract of DOI:10.1021/jo00244a012

The syntheses of the stereospecific deuteriated derivatives (2S,4R)- and (2S,4S)-<4-²H>homoserine lactone hydrochlorides, (2S,3R)-<3-²H>- and (2S,3S)-<2,3-²H2>homoserine lactone hydrochlorides, and (2S,3R,4R)-<3,4-²H2>- and (2S,3S,4S)-<2,3,4-²H3>homoserine lactone hydrochlorides as well as the homoserine derivatives themselves have been synthesized in eight simple steps from the appropriate aspartic acids via a route designed for maximal synthetic versatility.The enantiomeric excesses at carbon 4 of the deuteriated homoserines are R = 78percent (98percent ²H) and S = 82percent (98percent ²H) and at carbon 3 R = 100percent (98percent ²H2) and S = 100percent (95percent²H).