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Asymmetric Organocatalytic Formal Aza‐Michael Addition of Ammonia to Nitroalkenes
Author(s) -
Lykke Lennart,
Monge David,
Nielsen Martin,
Jørgensen Karl Anker
Publication year - 2010
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201002415
Subject(s) - michael reaction , thiourea , imine , ammonia , benzophenone , chemistry , nitro , organic chemistry , combinatorial chemistry , hydrolysis , catalysis , alkyl
The formal addition of ammonia to nitroalkenes, affording optically active β ‐ amino nitro compounds in high yields and enantioselectivities, is presented (see scheme). The approach is based on a novel thiourea‐catalyzed aza‐Michael reaction, by which benzophenone imine serves as a masked ammonia equivalent, which is released by hydrolysis.