Andersen chemistry with an α,β-unsaturated sulfinyl chloride: synthesis and Grignard reactions of homochiral cholesteryl (R)S-(E)-t-butylethenesulfinate

Autor:	Adrian L. Schwan, Rick R. Strickler
Rok vydání:	1999
Předmět:	Inorganic Chemistry Substitution reaction Enantiopure drug Stereospecificity Chemistry Yield (chemistry) Organic Chemistry medicine Organic chemistry Physical and Theoretical Chemistry Chloride Catalysis medicine.drug
Zdroj:	Tetrahedron: Asymmetry. 10:4065-4069
ISSN:	0957-4166
Popis:	(−)-Cholesteryl ( R ) S -( E )- t -butylethenesulfinate 2 was prepared in enantiopure form through the reaction of ( E )- t -butylethenesulfinyl chloride and (−)-cholesterol in the presence of quinine (ca. 36% yield). Diastereomerically enriched versions of ( S )- 2 were prepared with d.e.s up to 75%. Grignard substitution reactions of 2 proceed with high stereospecificity to provide a new access to enantiomerically enriched ( E )-2- t -butylethenylaralkyl sulfoxides in good yield and excellent e.e.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_________::28447d5110b79ed68f0cf2187e180f87 https://doi.org/10.1016/s0957-4166(99)00439-5 Zobrazit plný text záznamu Full Text from ScienceDirect