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Enantioselective Friedel–Crafts Alkylation of Indoles with ( E )‐1‐Aryl‐4‐benzyloxybut‐2‐en‐1‐ones Catalyzed by an ( R )‐3,3′‐Br 2 BINOLate–Hafnium(IV) Complex
Author(s) -
Blay Gonzalo,
Fernández Isabel,
Muñoz M. Carmen,
Pedro José R.,
Vila Carlos
Publication year - 2013
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201201636
Subject(s) - chemistry , friedel–crafts reaction , stereocenter , enantioselective synthesis , indole test , aryl , moiety , alkylation , catalysis , medicinal chemistry , stereochemistry , derivative (finance) , organic chemistry , alkyl , financial economics , economics
A highly enantioselective Friedel–Crafts reaction of unprotected indoles with ( E )‐1‐aryl‐4‐benzyloxybut‐2‐en‐1‐ones catalyzed by a new chiral [Hf{( R )‐3,3′‐Br 2 ‐BINOL}(O t Bu) 2 ] 2 complex has been developed to functionalize the C‐3 position of the indole nucleus with a side chain bearing a 1,4‐difunctionalized moiety and a benzylic stereogenic center. The reaction proceeds in good to excellent yields and excellent enantioselectivities (up to 97 % ee ). The usefulness of this approach was illustrated with the synthesis of a tryptophol derivative.