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Synergistic Diastereo‐ and Enantioselective Functionalization of Unactivated Alkyl Quinolines with α,β‐Unsaturated Aldehydes
Author(s) -
Meazza Marta,
Tur Fernando,
Hammer Niels,
Jørgensen Karl Anker
Publication year - 2017
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.201611306
Subject(s) - chemistry , electrophile , alkyl , quinoline , iminium , enantioselective synthesis , surface modification , stereoselectivity , catalysis , lewis acids and bases , adduct , organocatalysis , combinatorial chemistry , organic chemistry
A novel alkyl functionalization of unactivated alkyl quinolines has been developed combining InCl 3 activation with organocatalytic activation of α,β‐unsaturated aldehydes in a synergistic fashion. The reaction proceeds in a highly stereoselective manner as a sequence involving two consecutive synergistic catalytic cycles (Lewis acid‐ and iminium ion‐catalyzed) and requires neither pre‐activated alkyl quinoline substrates with electron‐withdrawing substituents nor highly activated electrophiles. The reaction provides selectively double‐ or mono‐addition products in good yields and high to excellent stereoselectivities. Furthermore, based on spectroscopic and labelling experiments, the mechanisms for the reactions are discussed.