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Catalytic Asymmetric N‐Alkylation of Indoles and Carbazoles through 1,6‐Conjugate Addition of Aza‐ para ‐quinone Methides
Author(s) -
Chen Min,
Sun Jianwei
Publication year - 2017
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201701947
Subject(s) - chemistry , alkylation , carbazole , indole test , nucleophile , catalysis , reagent , enantioselective synthesis , organocatalysis , phosphoric acid , quinone , conjugate , combinatorial chemistry , intermolecular force , functional group , organic chemistry , molecule , mathematical analysis , mathematics , polymer
Catalytic asymmetric N‐alkylation of indoles and carbazoles represents a family of important but underdeveloped reactions. Herein, we describe a new organocatalytic strategy in which in situ generated aza‐ para ‐quinone methides are employed as the alkylating reagent. With the proper choice of a chiral phosphoric acid and an N‐protective group, the intermolecular C−N bond formation with various indole and carbazole nucleophiles proceeded efficiently under mild conditions with excellent enantioselectivity and functional‐group compatibility. Control experiments and kinetic studies provided important insight into the reaction mechanism.