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Aza‐Baylis–Hillman Reactions of N ‐(Arylmethylene)diphenylphosphinamides with Activated Olefins in the Presence of Various Lewis Bases
Author(s) -
Shi Min,
Zhao GuiLing
Publication year - 2004
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.200404081
Subject(s) - methyl vinyl ketone , chemistry , methyl acrylate , lewis acids and bases , ketone , acrylonitrile , adduct , phosphine , baylis–hillman reaction , organic chemistry , methyl ketone , catalysis , polymer chemistry , acrylate , copolymer , polymer
The aza‐Baylis–Hillman reactions of N ‐(arylmethylene)diphenylphosphinamides with methyl vinyl ketone (MVK), methyl acrylate, acrylonitrile, ethyl vinyl ketone (EVK), phenyl vinyl ketone (PVK), phenyl acrylate, 2‐cyclopenten‐1‐one, 2‐cyclohexen‐1‐one have been systemically investigated in the presence of various Lewis bases. The Lewis base and solvent effects in these reactions have been discussed. A new class of double aza‐Baylis–Hillman reactions (in some cases exclusively) and their further transformations including catalytic, asymmetric version in the presence of chiral nitrogen and phosphine Lewis bases have been disclosed in this paper.