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Stereoselective Synthesis of Polysubstituted Alkenes through a Phosphine‐Mediated Three‐Component System of Aldehydes, α‐Halo Carbonyl Compounds, and Terminal Alkenes
Author(s) -
Liu DaNeng,
Tian ShiKai
Publication year - 2009
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.200900177
Subject(s) - stereoselectivity , chemistry , phosphine , wittig reaction , alkene , aldehyde , acrylamide , methyl acrylate , organic chemistry , acrylate , selectivity , component (thermodynamics) , medicinal chemistry , catalysis , copolymer , polymer , physics , monomer , thermodynamics
Geometrical control : PPh 3 and methyl acrylate (or acrylamide) are able to mediate the one‐pot Wittig reaction of aldehydes with α‐halo carbonyl compounds for the synthesis of 1,2‐disubstituted and trisubstituted alkenes in an excellent stereoselective fashion. Furthermore, the first one‐pot, three‐component reaction of aldehydes, α‐halo acetates, and terminal alkenes has been developed in the presence of PPh 3 to produce trisubstituted alkenes with excellent E selectivity (see scheme).