John M. Schwab

Stereochemical course of the hydration reaction catalysed by β-hydroxydecanoylthioester dehydrase

Enzyme-catalysed hydration of the N-acetylcysteamine thioester of (E)-dec-2-enoic acid to the corresponding thioester of (R)-3-hydroxydecanoic acid proceeds in a syn fashion, with protonation on the si face at substrate C-2.

Chirally-labelled oxirane

(R,R)- and (S,S)-[1,2-2H2]oxiranes have been synthesized from prop-2-yn-1-ol, the key step being asymmetric epoxidation of (E)-3-(triphenylsilyl)[2,3-2H2]prop-2-en-1-ol.

A facile synthesis of (2RS,3S,4S)-[3,4-2H2]homoserine lactone

Homoserine lactone chirally labelled with deuterium at C-3 and C-4 has been synthesized in two steps, starting from chirally labelled oxirane.