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Highly Enantioselective Friedel–Crafts Reaction of 4,7‐Dihydroindoles with β,γ‐Unsaturated α‐Keto Esters by Chiral Brønsted Acids
Author(s) -
Zeng Mi,
Kang Qiang,
He QingLi,
You ShuLi
Publication year - 2008
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.200800523
Subject(s) - friedel–crafts reaction , chemistry , alkylation , indole test , enantioselective synthesis , organic chemistry , derivative (finance) , brønsted–lowry acid–base theory , catalysis , medicinal chemistry , financial economics , economics
A highly efficient Friedel–Crafts reaction of 4,7‐dihydroindoles with β,γ‐unsaturated α‐keto esters by a chiral N ‐triflyl phosphoramide was realized, affording the 2‐substituted 4,7‐dihydroindoles with up to 98% ee for a wide range of substrates. The Friedel–Crafts alkylation together with a subsequent oxidation of the product with p ‐benzoquinone led to a 2‐alkylated indole derivative in 98% ee .