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Enantioselective Nitroso Aldol Reaction Catalyzed by a Chiral Phosphine–Silver Complex
Author(s) -
Yanagisawa Akira,
Lin Yuqin,
Takeishi Akihiro,
Yoshida Kazuhiro
Publication year - 2016
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.201601143
Subject(s) - chemistry , aldol reaction , enantioselective synthesis , phosphine , nitroso , catalysis , nitroso compounds , quinoxaline , methanol , medicinal chemistry , organic chemistry , optically active , base (topology) , mathematical analysis , mathematics
A catalytic asymmetric O ‐nitroso aldol reaction of alkenyl trifluoroacetates with nitrosoarenes was achieved by using QuinoxP* · AgOAc [( R , R )‐QuinoxP* = (–)‐( R , R )‐2,3‐bis( tert ‐butylmethylphosphino)quinoxaline] as the chiral precatalyst and N , N ‐diisopropylethylamine as the base precatalyst in the presence of methanol. Optically active α‐aminooxy ketones with up to 99 % ee were regioselectively obtained in moderate to high yields by the in situ generated chiral silver enolates.