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2007•OrganometallicsRequires access

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

Daniel Carmona, M.P. Lamata, Fernando Viguri, Ricardo M. Rodriguez, Carmen Barba, Fernando J. Lahoz, M. Luisa Martín, Luis A. Oro, Luis Salvatella

Open publisher page 17 citations

Abstract

The Diels−Alder reaction between methacrolein and cyclopentadiene catalyzed by [(η 5 -C 5 Me 5 )Ir{( R )-Prophos}(methacrolein)][SbF 6 ] 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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What this paper is about

The Diels−Alder reaction between methacrolein and cyclopentadiene catalyzed by [(η 5 -C 5 Me 5 )Ir{( R )-Prophos}(methacrolein)][SbF 6 ] 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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Available abstract

The Diels−Alder reaction between methacrolein and cyclopentadiene catalyzed by [(η 5 -C 5 Me 5 )Ir{( R )-Prophos}(methacrolein)][SbF 6 ] 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.

Key concepts: Methacrolein, Cyclopentadiene, Chemistry, Lewis acids and bases, Chiral Lewis acid, Enantioselective synthesis, Diels–Alder reaction, Stereochemistry

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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 — Research Paper | ScholarLens