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Synthesis and reduction of 2,2‐diaryl‐1‐nitroethylenes by using a chiral and a non chiral NADH model in the pyrrolopyridine series
Author(s) -
Levacher Vincent,
Valque Claude,
Coupa Sophie,
Dupas Georges,
Quéguiner Guy,
Bourguig Jean
Publication year - 1996
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.5570330435
Subject(s) - nitroethane , chemistry , yield (engineering) , reduction (mathematics) , medicinal chemistry , nitromethane , organic chemistry , mathematics , materials science , geometry , metallurgy
Abstract Reduction of 2,2‐diphenyl‐1‐nitroethylene ( 1 ) and 2‐(2‐pyridyl)‐2‐phenyl‐1‐nitroethylene ( 5 ) is achieved by using the NADH model in the pyrrolopyridine series 2a to give 2,2‐diphenyl‐1‐nitroethane ( 3 ) and 2‐(2‐pyridyl)‐2‐phenyl‐1‐nitroethane ( 7 ) respectively in 40% yield. The asymmetric reduction of 2‐(2‐pyridyl)‐2‐phenyl‐1‐nitroethylene by the chiral NADH model 2b is studied. Thus, 2‐(2‐pyridyl)‐2‐phenyl‐1‐nitroethane ( 7 ) is obtained in 15 to 32% yield. The stereocontrol of the reduction proved to be dependent on the amount of magnesium ions.