New S,O-Acetals from (1R)-(-)-Myrtenal as Chiral Auxiliaries in Nucleophilic Additions

Autor:	L. Gerardo Zepeda, Joaquín Tamariz, Selene Lagunas-Rivera, Luis Chacón-García, Salvador Pérez-Estrada, Pedro Joseph-Nathan, M. Elena Vargas-Dı́az
Rok vydání:	2004
Předmět:	Chemistry Organic Chemistry General Medicine Biochemistry Medicinal chemistry Hydrolysis Column chromatography Nucleophile Yield (chemistry) Reagent Drug Discovery Organic chemistry Enantiomer Enantiomeric excess
Zdroj:	ChemInform. 35
ISSN:	1522-2667 0931-7597
Popis:	Treatment of hydroxythiol 4 with α,α-diethoxyacetophenone at room temperature yielded a mixture of epimeric S,O-acetals 6 and 7 (1:4, 92% yield), which were efficiently separated by flash chromatography. The OTBS derivatives 8 and 9 were treated with several Grignard reagents to afford carbinols 10 and 13 respectively (85–99% yield, >95% dr). After successive hydrolysis and reduction of 10 and 13 it is possible to obtain either enantiomer of diols 16 in high optical purity (>95% er).
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_dedup___::abc80223de498cb132fad3a7369f82d4 https://doi.org/10.1002/chin.200424086 Zobrazit plný text záznamu Plný text