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Switching the N ‐Alkylation of Arylamines with Benzyl Alcohols to Imine Formation Enables the One‐Pot Synthesis of Enantioenriched α‐ N ‐Alkylaminophosphonates
Author(s) -
Hofmann Natalie,
Hultzsch Kai C.
Publication year - 2019
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.201900209
Subject(s) - chemistry , alkylation , imine , phosphoric acid , organic chemistry , condensation , nitrile , amine gas treating , combinatorial chemistry , surface modification , enantioselective synthesis , catalysis , physics , thermodynamics
The selective N ‐alkylation of anilines with benzylic alcohols can be switched in favor of the dehydrogenative condensation process using the nitrile‐ligated Knölker's complex by conducting the reaction either in a closed system under inert conditions, or in an open system in air. The selective formation of imines, containing reactive C=N bonds, provides an opportunity towards further functionalization. Indeed, a one‐pot three‐component condensation of alcohols, amines and phosphites, promoted by an iron‐based Knölker‐type complex in combination with a chiral BINOL‐based phosphoric acid, provides access to enantioenriched α‐ N ‐alkylaminophosphonates.