Synthesis of chirally deuteriated phthalimido-propanols and evaluation of their absolute stereochemistry

PC Prabhakaran, SJ Gould, GR Orr…

Index: Prabhakaran,P.C.; Gould,S.J.; Orr,G.R. Journal of the American Chemical Society, 1988 , vol. 110, p. 5779

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Citation Number: 25

Abstract

Results One synthesis of 4 applied a purely chemical route whereby chirality was introduced by stereospecific reduction of the deuteriated aldehyde 6a (Figure 1). Commercially available ethyl 3-chloropropionate, 5, was reduced with LiAIDl and the resulting 3-chloro-1, 1-dideuteriopropanol was converted into 1, l-di-deuteriophthalimidopropanol in 50-55% overall yield. This product was oxidized to deuterio aldehyde 6a, by using Swern's ...