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Planar‐Chiral Cyclopentadienyl‐Ruthenium‐Catalyzed Regio‐ and Enantioselective Asymmetric Allylic Alkylation of Silyl Enolates under Unusually Mild Conditions
Author(s) -
Kanbayashi Naoya,
Yamazawa Arisa,
Takii Koichiro,
Okamura Takaaki,
Onitsuka Kiyotaka
Publication year - 2016
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.201500970
Subject(s) - chemistry , allylic rearrangement , enantioselective synthesis , tsuji–trost reaction , regioselectivity , cyclopentadienyl complex , silylation , ruthenium , nucleophile , alkylation , aldehyde , medicinal chemistry , catalysis , organic chemistry
We report the asymmetric allylic alkylation of allylic chlorides with silyl enolates as a carbon nucleophile using a planar‐chiral cyclopentadienyl‐ruthenium (Cp′Ru) catalyst. The reaction proceeds under unusually mild conditions to give the desired branched products with complete regioselectivity and high enantioselectivity, and reactive functional groups, such as aldehyde, can be tolerated. In this reaction system, Cp′Ru plays an important role in activating both silyl enolate and allylic chloride.