title: Advances in nucleophilic phosphine catalysis of alkenes, allenes, alkynes, and MBHADs.
abstract: In nucleophilic phosphine catalysis, tertiary phosphines undergo conjugate additions to activated carbon-carbon multiple bonds to form β-phosphonium enolates, β-phosphonium dienolates, β-phosphonium enoates, and vinyl phosphonium ylides as intermediates. When these reactive zwitterionic species react with nucleophiles and electrophiles, they may generate carbo- and heterocycles with multifarious molecular architectures. This article describes the reactivities of these phosphonium zwitterions, the applications of phosphine catalysis in the syntheses of biologically active compounds and natural products, and recent developments in the enantioselective phosphine catalysis.
authors.affiliation: Department of Chemistry and Biochemistry, University of California, Los Angeles, California 90095-1569, USA. Ohyun@chem.ucla.edu.
authors.forename: Yi Chiao
authors.initials: YC
authors.lastname: Fan
authors.forename: Ohyun
authors.initials: O
authors.lastname: Kwon
mesh_terms: D000466:Alkadienes / Q000737:chemistry*; D000475:Alkenes / Q000737:chemistry*; D000480:Alkynes / Q000737:chemistry*; D002384:Catalysis; D010720:Phosphines / Q000737:chemistry*
chemical_list: D000466:Alkadienes; D000475:Alkenes; D000480:Alkynes; D010720:Phosphines; C025947:propadiene; C044646:phosphine