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Activation of Alkynylzinc Reagents by a Hemiaminal‐Driven Catalytic Microenvironment
Author(s) -
St. Denis Jeffrey D.,
Liew Sean K.,
Scully Conor C. G.,
Yudin Andrei K.
Publication year - 2017
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.201601554
Subject(s) - iminium , chemistry , alkyne , hemiaminal , regioselectivity , aziridine , aldehyde , hydroamination , intramolecular force , catalytic cycle , catalysis , reagent , combinatorial chemistry , ring (chemistry) , stereochemistry , organic chemistry
1,2‐Aziridinyl propargylic amines have been obtained through a zinc‐catalyzed multicomponent reaction. This process relies on the dimeric amino aldehyde assembly orchestrating the intramolecular 1,2‐alkyne addition to an iminium ion. The resulting products can be readily elaborated through regioselective aziridine ring opening. A catalytic cycle and stereochemical rationale for the highly anti ‐selective alkyne addition is proposed.