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 in | Organic letters Vol. 12; no. 24; pp. 5620 - 5623 |
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Main Authors | , , , , , , |
Format | Journal Article |
Language | English |
Published |
WASHINGTON
American Chemical Society
17.12.2010
Amer Chemical Soc |
Subjects | |
Online Access | Get full text |
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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. |
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Bibliography: | ObjectType-Article-1 SourceType-Scholarly Journals-1 ObjectType-Feature-2 content type line 23 |
ISSN: | 1523-7060 1523-7052 |
DOI: | 10.1021/ol102283c |