Catalytic and asymmetric variations, enones, enynes, and allene as other starting materials, and numerous applications in natural product synthesis are all evidence of the diversity of the Pauson-Khand reaction [Eq. (a)], which now definitely counts among the standard tools of organic synthesis.

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New Developments in the Pauson-Khand Reaction.

Five membered carbocycles are important building blocks for many biologically active molecules. Moreover, substituted cyclopentenones (e.g. cyclopentenone prostaglandins) exhibit characteristic biological activity. The efficiency and atom economy of the Pauson-Khand reaction render this process potentially one of the most attractive methods for the synthesis of such compounds. Although it was discovered in its intermolecular form, the scope of the intermolecular Pauson-Khand reaction has always been limited by the poor reactivity and selectivity of the alkene component. The past decade, especially the last three years, has seen concerted efforts to broaden the scope of this reaction. In this overview, we provide a comprehensive and critical coverage of the intermolecular Pauson-Khand reaction based on the reactivity characteristics of different classes of alkenes and a rationalization of successes and misfortunes in this area.

The intermolecular Pauson-Khand reaction.

Synthesis of cyclopentitols by ring-closing approaches.

The Concept of Transient Chirality in the Stereoselective Synthesis of Functionalized Cycloalkenes Applying the Retro-Diels−Alder Methodology

The asymmetric pauson-khand reaction. a review

Practical asymmetric version of the intermolecular pauson-khand reaction

The first practical asymmetric version of the intermolecular Pauson-Khand reaction has been developed based on novel chiral (non-racemic) alkoxy acetylene dicobalt hexacarbonyl complexes. The major adduct from (1R, 2S)-2-phenylcyclohexyloxyethyne and norbornadiene, isolated in 58% yield, is shown to be useful for obtaining chiral 4-substituted 2-cyclopentenones.

Nathalie Kardos

Papers

Practical asymmetric version of the intermolecular pauson-khand reaction

Practical Asymmetric Version of the Intermolecular Pauson-Khand Reaction.