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Enantioselective Annulations for Dihydroquinolones by in Situ Generation of Azolium Enolates
Author(s) -
Anna Lee,
Ashkaan Younai,
Christopher K. Price,
Javier Izquierdo,
Rama K. Mishra,
Karl A. Scheidt
Publication year - 2014
Publication title -
journal of the american chemical society
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 7.115
H-Index - 612
eISSN - 1520-5126
pISSN - 0002-7863
DOI - 10.1021/ja505880r
Subject(s) - chemistry , enantioselective synthesis , annulation , in situ , catalysis , dual (grammatical number) , quinone , quinone methide , combinatorial chemistry , stereochemistry , organic chemistry , art , literature
A convergent, catalytic asymmetric formal [4 + 2] annulation for the synthesis of dihydroquinolones has been developed. Carboxylic acids can be employed as precursors to NHC enolates through an in situ activation strategy. Simultaneous generation of a reactive aza-o-quinone methide under the basic conditions employed for NHC generation leads to a dual activation approach.

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