Stereospecific Grignard reactions of cholesteryl 1-alkenesulfinate esters: Application of the Andersen Protocol to the preparation of non-racemic α,β-unsaturated sulfoxides

Autor:	Adrian L. Schwan, Craig C Humber, Rick R. Strickler, John M. Motto
Rok vydání:	2003
Předmět:	chemistry.chemical_compound Stereospecificity chemistry Reagent Organic Chemistry Organic chemistry chemistry.chemical_element General Chemistry Benzene Sulfur Catalysis
Zdroj:	Canadian Journal of Chemistry. 81:423-430
ISSN:	1480-3291 0008-4042
Popis:	Enantiomerically enriched α,β-unsaturated sulfinate esters of (–)-cholesterol undergo stereospecific substitutions at sulfur when treated in benzene at 6°C with Grignard reagents. Sulfoxides with ees of 85–99.5% are obtained when enantiopure sulfinates are used. The substitution reactions proceed with inversion of sulfur configuration. Enantiomerically pure cholesteryl (E)-2-carbomethoxyethenesulfinate is not a suitable reactant under the Grignard reaction conditions. It is suggested that the ester group induces unwanted reactions significantly lowering both the yield and sulfur stereogenicity.Key words: sulfinate, sulfoxide, Grignard reagents, stereospecific, unsaturated.
Databáze:	OpenAIRE
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