Asymmetric alkylation of 3-substituted benzofuran-2(3H)-ones

[Display omitted] An enantioselective alkylation reaction of 3-substituted benzofuran-2(3H)-ones catalyzed by a chiral biscinchona alkaloid catalyst combined with TsOH·H2O was developed. The corresponding products, containing all carbon quaternary centers at the C3-positions of the benzofuran-2-ones...

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Bibliographic Details
Published inTetrahedron letters Vol. 56; no. 44; pp. 6112 - 6115
Main Authors Luo, Chao, Zhang, Enge, Li, Xin
Format Journal Article
LanguageEnglish
Published OXFORD Elsevier Ltd 28.10.2015
Elsevier
Subjects
Alkylation
Asymmetric catalysis
Benzofuran-2(3H)-one
Chemistry
Chemistry, Organic
Cinchona alkaloid
Physical Sciences
Quaternary center
Science & Technology
Benzofuran-2(3H)-one
Cinchona alkaloid
Quaternary center
Asymmetric catalysis
Alkylation
DAPHNODORIN
ACID
ANNULATION
MICHAEL ADDITION-REACTIONS
BENZOFURAN-2-ONES
FACILE SYNTHESIS
GAMMA-ALKYLATION
CONSTRUCTION
DERIVATIVES
CONSTITUENTS
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Summary:[Display omitted] An enantioselective alkylation reaction of 3-substituted benzofuran-2(3H)-ones catalyzed by a chiral biscinchona alkaloid catalyst combined with TsOH·H2O was developed. The corresponding products, containing all carbon quaternary centers at the C3-positions of the benzofuran-2-ones, were obtained in moderate to good yields (up to 89%) with good enantioselectivities (up to 83% ee).
ISSN:0040-4039
1873-3581
DOI:10.1016/j.tetlet.2015.09.087