The Journal of Organic Chemistry

Synthesis of (4R)-D, L-[4-2H]-and (4S)-D, L-[42H] homoserine lactones

DM Kalvin, RW Woodard

Index: Kalvin, Douglas M.; Woodard, Ronald W. Journal of Organic Chemistry, 1985 , vol. 50, # 13 p. 2259 - 2263

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Citation Number: 38

Abstract

aluminum deuteride (DIBAL-D) in 75% yield as described by Kalvin et al. l0 The mass spectral analysis of compound 4 showed 99.9% deuterium incorporation. Deuterio aldehyde 4 (Scheme 11) was reduced in a stereospecific manner with (R)-and (S)-Alpine boranes1'to yield the chiral S and R alcohols 5a (73%) and 5b (75%), respectively. Midland et al. 12Gb and other investigatorslkpd have prepared a variety of chiral primary deuterio alcohols in ...