Org Lett. 2010 Dec 17;12(24):5620-3. Epub 2010 Nov 17.

Regioselectivity in intermolecular Pauson-Khand reactions of dissymmetric fluorinated alkynes.

Kizirian JC, Aiguabella N, Pesquer A, Fustero S, Bello P, Verdaguer X, Riera A.

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Unitat de Recerca en Síntesi Asimètrica (URSA-PCB), Institute for Research in Biomedicine (IRB) and Departament de Química Orgànica, Universitat de Barcelona, c/Baldiri Reixac, 10, E-0 8028 Barcelona, Spain. jean-claude.kizirian@univ-tours.fr

Abstract

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.

PMID:: 21082812; [PubMed - indexed for MEDLINE]

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Research Support, Non-U.S. Gov't

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Alkynes

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