The Asymmetric Pauson-Khand Reaction. A Review

Ingate, S. T.; Marco-Contellers, J.

doi:10.1080/00304949809355274

Cited by 109 publications

(11 citation statements)

References 70 publications

(4 reference statements)

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“…Additionally, it is tolerant to a broad variety of functional groups, such as alcohols, ethers, thioethers, esters, nitriles, amines, amides, sulfonamides, etc. Therefore, the transformation has received great attention over the last few decades, and a wide number of records appeared in the literature, including a series of reviews. − The asymmetric versions are efficiently accomplished by applying a number of methods to introduce chirality. Depending on the stereochemistry of the reagents, the protocols can be divided into two general categories based on chiral auxiliaries attached either to the alkene or to the alkyne, or starting from achiral precursors.…”

Section: Introduction Of Chirality During the Generation Of The Cyclo...mentioning

confidence: 99%

Synthesis of Chiral Cyclopentenones

et al. 2016

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The cyclopentenone unit is a very powerful synthon for the synthesis of a variety of bioactive target molecules. This is due to the broad diversity of chemical modifications available for the enone structural motif. In particular, chiral cyclopentenones are important precursors in the asymmetric synthesis of target chiral molecules. This Review provides an overview of reported methods for enantioselective and asymmetric syntheses of cyclopentenones, including chemical and enzymatic resolution, asymmetric synthesis via Pauson-Khand reaction, Nazarov cyclization and organocatalyzed reactions, asymmetric functionalization of the existing cyclopentenone unit, and functionalization of chiral building blocks.

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Section: Introduction Of Chirality During the Generation Of The Cyclo...mentioning

confidence: 99%

Synthesis of Chiral Cyclopentenones

et al. 2016

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“…The transition metal-mediated cyclization of an enyne with carbon monoxide, a Pauson−Khand type reaction, is an efficient method for the construction of bicyclic cyclopentenones . We have previously reported a catalytic version of this reaction utilizing commercially available Cp 2 Ti(CO) 2 ( 1 ). , It was subsequently shown that an enantiomerically pure analogue of the titanocene complex, ( S,S )-(EBTHI)Ti(CO) 2 ( 2 ) (EBTHI = ethylene-1,2-bis(η 5 -4,5,6,7-tetrahydro-1-indenyl), generated in situ from ( S,S )(EBTHI)TiMe 2 ( 3 ), can serve as a catalyst for this reaction . Using this method, a variety of 1,6-enynes could be cyclized with high levels of enantioselectivity (Scheme ) …”

Section: Introductionmentioning

confidence: 99%

Catalytic Asymmetric Cyclocarbonylation of Nitrogen-Containing Enynes

Sturla

Buchwald

1999

J. Org. Chem.

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The asymmetric Pauson-Khand type cyclization of nitrogen-containing enynes using carbon monoxide and a catalytic amount of (EBTHI)TiMe(2) was examined. The influence of the nitrogen substituent and the concentration of the catalyst on the enantioselectivity of this cyclization was explored, and it has been found that enynes with an octyl-, benzyl-, or allylamino group, positioned beta to the alkyne and the olefin, are cyclized with a high degree of enantioselectivity. Substrates with either bulky and/or electron-withdrawing nitrogen substituents are converted to products in low to moderate enantioselectivity.

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“…Based on the frequent application of the intramolecular Pauson−Khand reaction in the total synthesis of natural products in racemic form, the availability of an asymmetric variant would be a useful tool for the organic chemist. Much effort has been devoted toward this end in the past decade, and the approaches toward a stoichiometric intramolecular version fall into two basic categories: the diastereoselective cyclization of optically active enynes and that of enynes equipped with chiral auxiliaries; this field has been the subject of a recent review …”

Section: Introductionmentioning

confidence: 99%

An Intramolecular Titanium-Catalyzed Asymmetric Pauson−Khand Type Reaction¹

1999

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The development of the first catalytic asymmetric Pauson−Khand type cyclization of enynes is described. The active catalyst, (S,S)-(EBTHI)Ti(CO)2 (1), is generated in situ from (S,S)-(EBTHI)TiMe2 (2). A variety of 1,6-enynes can be converted to the corresponding cyclopentenones in high yield (70−94%) with excellent ee's (87−96%). Limitations of the catalyst with respect to substrate structure are discussed. The absolute configurations of several of the enone products have been ascertained, and these assignments represent a reversal with respect to an assignment in the initial report. A rationale for the sense and levels of enantioselectivity for this catalyst is proposed.

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The Asymmetric Pauson-Khand Reaction. A Review

Cited by 109 publications

References 70 publications

Synthesis of Chiral Cyclopentenones

Synthesis of Chiral Cyclopentenones

Catalytic Asymmetric Cyclocarbonylation of Nitrogen-Containing Enynes

An Intramolecular Titanium-Catalyzed Asymmetric Pauson−Khand Type Reaction¹

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The Asymmetric Pauson-Khand Reaction. A Review

Cited by 109 publications

References 70 publications

Synthesis of Chiral Cyclopentenones

Synthesis of Chiral Cyclopentenones

Catalytic Asymmetric Cyclocarbonylation of Nitrogen-Containing Enynes

An Intramolecular Titanium-Catalyzed Asymmetric Pauson−Khand Type Reaction1

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An Intramolecular Titanium-Catalyzed Asymmetric Pauson−Khand Type Reaction¹