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Industrial Synthesis of (+)‐ cis ‐Methyl Dihydrojasmonate by Enantioselective Catalytic Hydrogenation; Identification of the Precatalyst [Ru((−)‐Me‐DuPHOS)(H)( η 6 ‐1,3,5‐cyclooctatriene)](BF 4 )
Author(s) -
Dobbs Daniel A.,
Vanhessche Koenraad P. M.,
Brazi Eric,
Rautenstrauch Valentin,
Lenoir JeanYves,
Genêt JeanPierre,
Wiles Jason,
Bergens Steven H.
Publication year - 2000
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/1521-3773(20000602)39:11<1992::aid-anie1992>3.0.co;2-w
Subject(s) - enantioselective synthesis , catalysis , chemistry , identification (biology) , combinatorial chemistry , organic chemistry , biology , botany
Prototypes of new families of precatalysts and catalysts , [Ru((−)‐Me‐DuPHOS)(H)( η 6 ‐1,3,5‐cyclooctatriene)](BF 4 ) and the derived “[Ru((−)‐Me‐DuPHOS)(H)(sol)](BF 4 )”, are presented. They are used in an industrial, catalytic, enantioselective hydrogenation that leads to (+)‐ cis ‐methyl dihydrojasmonate [Eq. (1)]. This stereoisomer is the odorant component of an important, large volume perfumery chemical. P−P=Diphosphane ligand (for example, Me‐DuPHOS=1,2‐bis((2 R ,5 R )‐2,5‐dimethylphospholanyl)benzene); sol=solvent.