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Enantioselective Organocatalyzed aza ‐Michael Addition Reaction of 2‐Hydroxybenzophenone Imines to Nitroolefins under Batch and Flow Conditions
Author(s) -
GuerreroCorella Andrea,
ValleAmores Miguel A.,
Fraile Alberto,
Alemán José
Publication year - 2021
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.202100635
Subject(s) - michael reaction , enantioselective synthesis , chemistry , imine , intramolecular force , moiety , nucleophile , organocatalysis , hydrogen bond , combinatorial chemistry , organic chemistry , catalysis , molecule
Herein, an asymmetric organocatalytic aza ‐Michael addition reaction of ketimines to nitroolefins is presented. The use of 2‐hydroxybenzophenone imine improves the enantioselective addition of N ‐centered nucleophiles to nitroalkenes by means of intramolecular hydrogen bond formation at the imine moiety. Moreover, the versatility of the process is demonstrated under both batch and flow conditions, showing the synthesis of a large variety of nitroamine derivatives with excellent yields and enantioselectivities. In addition, we applied this methodology to the formal synthesis of VNI, a drug‐like scaffold for the treatment of Chagas disease.