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Complete Characterization of a Chiral Lewis Acid−Product Complex for the Enantioselective Diels−Alder Reaction between Methacrolein and Cyclopentadiene: Mechanistic Considerations

Daniel Carmona,*^† M. Pilar Lamata,*^† Fernando Viguri,^† Ricardo Rodríguez,^† Carmen Barba,^† Fernando J. Lahoz,^† M. Luisa Martín,^† Luis A. Oro,^† and Luis Salvatella^‡

Departamento de Qumica Inorgnica and Departamento de Qumica Orgnica, Instituto Universitario de Catlisis Homognea, Instituto de Ciencia de Materiales de Aragn, Universidad de Zaragoza-Consejo Superior de Investigaciones Cientficas, 50009 Zaragoza, Spain

Organometallics, 2007, 26 (25), pp 6493–6496

DOI: 10.1021/om700717e

Publication Date (Web): November 7, 2007

Authors to whom all correspondence should be directed. E-mail: dcarmona@unizar.es; plamata@unizar.es. Fax number: 34 + 976 761187.

†

Departamento de Química Inorgánica.

‡

Departamento de Química Orgánica.

Abstract

The Diels−Alder reaction between methacrolein and cyclopentadiene catalyzed by [(η⁵-C₅Me₅)Ir{(R)-Prophos}(methacrolein)][SbF₆]₂ is inhibited by the products, this feature allowing, for the first time, the spectroscopic and crystallographic characterization of the major Lewis acid−product intermediate involving an enal as a dienophile.

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