Asymmetric alkylation reaction of α-fluorotetralone under phase-transfer catalyzed conditions

The catalytic asymmetric alkylation reaction of α-fluorotetralones promoted by a chiral quaternary ammonium salt derived from cinchonine under phase-transfer catalyzed conditions was described. The reaction proceeded smoothly to give the desired products with up to 91 % ee. This methodology provides...

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Bibliographic Details
Published inTetrahedron letters Vol. 40; no. 37; pp. 6785 - 6789
Main Authors Arai, Shigeru, Oku, Makoto, Ishida, Toshimasa, Shioiri, Takayuki
Format Journal Article
LanguageEnglish
Published OXFORD Elsevier Ltd 10.09.1999
Elsevier
Subjects
alkylation
asymmetric synthesis
catalysts
Chemistry
Chemistry, Organic
phase transfer
Physical Sciences
Science & Technology
alkylation
asymmetric synthesis
catalysts
phase transfer
SALT
ENANTIOSELECTIVE FLUORINATION
AGENTS
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Summary:The catalytic asymmetric alkylation reaction of α-fluorotetralones promoted by a chiral quaternary ammonium salt derived from cinchonine under phase-transfer catalyzed conditions was described. The reaction proceeded smoothly to give the desired products with up to 91 % ee. This methodology provides a practical protocol for the preparation of optically active fluoro compounds on a large scale. Graphic
ISSN:0040-4039
1873-3581
DOI:10.1016/S0040-4039(99)01282-4