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Asymmetric Catalytic Protonation of Silyl Enol Ethers with Chiral Palladium Complexes
Author(s) -
Sugiura Masaharu,
Nakai Takeshi
Publication year - 1997
Publication title -
angewandte chemie international edition in english
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 0570-0833
DOI - 10.1002/anie.199723661
Subject(s) - protonation , enol , palladium , chemistry , silylation , cationic polymerization , amine gas treating , catalysis , salt (chemistry) , medicinal chemistry , binap , enantioselective synthesis , photochemistry , organic chemistry , polymer chemistry , ion
Addition of amine is required to convert the chiral cationic palladium complex obtained from a silver salt and [PdCl 2 {(R)‐binap}] into an efficient asymmetric catalyst for the protonation of cyclic silyl enol ethers with water [Eq. (a)]. The effect of the amine is most likely based on selective deactivation of an initially formed Pd–binap comple. The “surviving” Pd species cause a reaction that is slower but proceeds with enhanced enantioselectivity.