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Versatile Access to Chiral Indolines by Catalytic Asymmetric Fischer Indolization
Author(s) -
Martínez Alberto,
Webber Matthew J.,
Müller Steffen,
List Benjamin
Publication year - 2013
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201301618
Subject(s) - stereocenter , enantioselective synthesis , nucleophile , vicinal , stereochemistry , ring (chemistry) , chemistry , catalysis , combinatorial chemistry , organic chemistry
“Fisching” for complexity : The chiral Brønsted acid ( R )‐STRIP catalyzes the asymmetric Fischer indolization of a range of monosubstituted cyclopentanones and cyclohexanones to give chiral fused indolines bearing a quaternary stereogenic center at the 3‐position. The method has been extended to include substrates bearing a tethered nucleophile, thus allowing for enantioselective indolization/ring‐closing cascades to complex propellanes featuring two vicinal quaternary stereocenters.