Enantioselective Brønsted Acid Catalysis in the Friedel-Crafts Reaction of Indoles with Secondary ortho-Hydroxybenzylic Alcohols
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http://www.thieme-connect.com/DOI/DOI?10.1055/s-0030-1259939
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资源简介：
The reaction of indole and various methyl-substituted indoles
with the title compounds was studied in the presence of chiral phosphoric
acids, which act as Brønsted acid catalysts. While yields were
generally high (>90%), significant enantioselectivities
(up to 77% ee) were only achieved for certain substrate-catalyst
combinations. In addition, a kinetic resolution of the starting
material was observed, which led to an enrichment of one chiral
alcohol to up to 68% ee after 76% conversion.
The Friedel-Crafts reaction is not stereospecific (no direct
SN2-type substitution), but rather is likely to proceed
via a cation, which is bound to the chiral Brønsted acid or
its anion in a close contact ion pair.
提供机构：
Georg Thieme Verlag, Stuttgart, New York
创建时间：
2011-11-30
