Silane-Controlled Diastereoselectivity in the Tris(pentafluorophenyl)borane-Catalyzed Reduction of α-Diketones to Silyl-Protected 1,2-Diols

Autor:	Andrea E. Kirby, Adrian Y. Houghton, Robert McDonald, D.J. Harrison, Lisa Rosenberg, Miranda K. Skjel
Rok vydání:	2009
Předmět:	Silanes Silylation Hydrosilylation Organic Chemistry Borane Biochemistry Medicinal chemistry chemistry.chemical_compound chemistry Reagent Electrophile Organic chemistry Tris(pentafluorophenyl)borane Disilane Physical and Theoretical Chemistry
Zdroj:	Organic Letters. 12:376-379
ISSN:	1523-7052 1523-7060
DOI:	10.1021/ol902451h
Popis:	B(C(6)F(5))(3)-catalyzed bis(hydrosilylation) of alpha-diketones can give high diastereomeric excess of either meso/anti (small silanes and disilane reagents) or dl/syn (bulky silanes) silyl-protected 1,2-diols. This easily tuned diastereoselectivity is rationalized based on the classic Felkin-Anh model applied to a mechanism relying on Si-H abstraction by the electrophilic borane reagent.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_dedup___::f8881f32be3073a370a08f02cf48b2e2 https://doi.org/10.1021/ol902451h Zobrazit plný text záznamu