G. Fronza et al., STEREOCHEMICAL FEATURES OF BAKERS-YEAST MEDIATED TRANSFORMATION OF RACEMIC AND ENANTIOMERICALLY PURE 2-DEUTERO-3-CHLOROPROPIOPHENONE, Tetrahedron : asymmetry, 4(8), 1993, pp. 1909-1916
Baker's yeast transforms (2R) and (2S) stereospecifically deuterated 3
-chloropropiophenone 11 and 12 into carbinols 14 and 15, and into prop
iophenone samples retaining, at position 2, 71% and 84% deuterium, res
pectively. Analogous experiments with randomly labelled ketone 10 gave
rise to a mixture of the carbinols 15 and 14 and to propiopheilone, t
hat retained 76% deuterium. The deuterium retention values in propioph
enone generated from randomly and stereospecifically labelled substrat
es 10, 11 and 12 indicate a non stereospecific elimination, accompanie
d, however, by a minor pathway in which H(R) is preferentially removed
.