Open AccessThe oxidation of organic sulphides by Mortierellaisabellina. 2. Effects of substituents on the stereochemistry of sulphoxide formation
Author(s) -
Herbert L. Holland,
Heike Pöpperl,
Ronald W. Ninniss,
P. Chinna Chenchaiah
Publication year - 1985
Publication title -
canadian journal of chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.323
H-Index - 68
eISSN - 1480-3291
pISSN - 0008-4042
DOI - 10.1139/v85-189
Subject(s) - chemistry , steric effects , enantiomer , stereoselectivity , alkyl , aryl , sulfur , stereochemistry , medicinal chemistry , ring (chemistry) , organic chemistry , catalysis
A series of para-substituted alkyl aryl sulphides has been transformed stereoselectively to the sulphoxide by incubation with the fungus Mortierellaisabellina. The enantiomeric purity of the products was dependent on the nature of substitution in the aromatic ring and at sulphur. Comparisons of the enantiomeric purities obtained from sulphides with para substituents of the same steric size but different electronic properties indicate that the stereoselectivity of S oxidation is susceptible to electron withdrawing or donating factors. This conclusion lends credence to a stepwise oxidation mechanism involving an electron deficient sulphur intermediate.