Regioselectivity in Intermolecular Pauson-Khand Reactions of Dissymmetric Fluorinated Alkynes

Stoichiometric and catalytic intermolecular Pauson−Khand reactions (PKRs) of dissymmetric fluorinated alkynes were performed, affording regioselectively α-fluorinated cyclopentenones. Ethyl 4,4,4-trifluorobutynoate was an excellent substrate; its reaction with norbornadiene gave the corresponding PK...

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Published inOrganic letters Vol. 12; no. 24; pp. 5620 - 5623
Main Authors Kizirian, Jean-Claude, Aiguabella, Nuria, Pesquer, Albert, Fustero, Santos, Bello, Paula, Verdaguer, Xavier, Riera, Antoni
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 17.12.2010
Amer Chemical Soc
Subjects
Alkynes - chemistry
Catalysis
Chemistry
Chemistry, Organic
Crystallography, X-Ray
Halogenation
Models, Molecular
Molecular Structure
Physical Sciences
Science & Technology
Stereoisomerism
NORBORNENE
LIGANDS
REGIOCHEMISTRY
COMPLEXES
PUPHOS
COORDINATION
BOND
DERIVATIVES
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Summary:Stoichiometric and catalytic intermolecular Pauson−Khand reactions (PKRs) of dissymmetric fluorinated alkynes were performed, affording regioselectively α-fluorinated cyclopentenones. Ethyl 4,4,4-trifluorobutynoate was an excellent substrate; its reaction with norbornadiene gave the corresponding PKR adduct in good yield and complete regioselectivity. Conjugate addition of nitroalkanes or cyanide to this adduct is stereospecific and entails concomitant loss of a trifluoromethyl group. This reaction can be exploited to prepare cyclopentenones featuring quaternary centers.
Bibliography:ObjectType-Article-1
SourceType-Scholarly Journals-1
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ISSN:1523-7060
1523-7052
DOI:10.1021/ol102283c