The bulky-headed oxidant hexadecyltrimethylammonium periodate affords the diastereomeric pairs, (Ss)-(+)/(Rs)-(+) and (Ss)-(-)/(Rs)-(-)-neomenthyl phenyl sulfoxides in stereochemically pure states with improved diastereomeric excess (48% diastereomeric excess [de]) as compared to its nonbulky counterpart, sodium metaperiodate (28% de) from respective (+)/(-)-neomenthyl phenyl sulfides. Steric effects involving the head group volume of hexadecyltrimethylammonium periodate is found to play a role in improving the diastereomeric ratio of the products. The two diastereomers can be readily separated by column chromatography. Absolute configuration at the sulfur center in (+)-neomenthyl phenyl sulfoxide was determined by single-crystal X-ray crystallography and found to be Ss. Relative configurations of other sulfoxides were assigned based on the configuration of (+)-neomenthyl phenyl sulfoxide.
Selective Oxidation of Sulfides to Sulfoxides with Cetyltrimethylammonium Periodate. -(CHAUDHARI, U. V.; DEOTA*, P. T.; Org. Prep. Proced. Int. 44 (2012) 4, 381-386, http://dx.
This describes attempts to synthesize compound (I), which is structurally related to Xeromphalinone E. -(SINGH, D.; CHAUDHARI, U. V.; DEOTA*, P. T.; Tetrahedron 70 (2014) 30, 4485-4493, http://dx.
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