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A Synthesis of Trisubstituted Alkenes by a Ru‐Catalyzed Addition
Author(s) -
Trost Barry M.,
Shen Hong C.,
Pinkerton Anthony B.
Publication year - 2002
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 - 10.1002/1521-3765(20020517)8:10<2341::aid-chem2341>3.0.co;2-a
Subject(s) - regioselectivity , steric effects , chemistry , hexafluorophosphate , catalysis , olefin fiber , ruthenium , medicinal chemistry , organic chemistry , ionic liquid
Catalyzed by ruthenium trisacetonitrile hexafluorophosphate 4 , the Alder‐ene type reaction of alkenes and internal alkynes provides an effective way to synthesize trisubstituted alkenes. Unlike most typical olefination protocols, this reaction is atom economical, and affords trisubstituted alkenes with defined olefin geometry. The regioselectivity can be explained invoking a steric argument based on the proposed mechanism. The first C−C bond formation generally involves sterically less hindered carbons of the alkenes and alkynes. Modest to very high regioselectivity can be achieved depending on the steric difference of the two substituents of alkynes.