Homochiral synthesis

Thompson MJ, Mekhalfia A, Jakeman DL, Phillips SEV, Phillips K, Porter J, et al. Homochiral synthesis of an aza analogue of S-adenosyl-L-methionine (AdoMet) and its binding to the E. coli methionine repressor protein (MetJ). Chem. Commun. 1996 791-792. 

Following this exploratory work, the Schmidt group (13) reported the first homochiral synthesis of methyl (-)- and (+)-nonactate using (S)-propylene oxide as the only enantiomerically pure starting material (Scheme 4). This gave the mixture of diastereoisomeric methyl nonactates 38, 39,40 and 41, all with the ( -configuration at C-8, and chromatographic separation provided 25% of the natural (-) ester 38. The mixture of the other three diastereoisomers (39+40+41) was converted by Walden inversion into a mixture of the same three compounds with C-8 inverted, from which (+)-methyl (25,35,6R,8/J)-nonactate 44 could be isolated in approximately the same amount as its enantiomer 38. 

A short homochiral synthesis of substituted vinyl pyrrolidines by a reductive ring opening-reductive amination sequence, followed by spontaneous displacement of benzoate has been reported (Scheme 9)/ ... 

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