A Dual-Function, Highly Efficient Chiral Controller for Stereoselective Intermolecular Pauson-Khand Reactions

Verdaguer, Xavier; Moyano, Albert; Pericàs, Miquel À.; Riéra, Antoni; Bernardes, Vania; Greene, Andrew E.; Álvarez‐Larena, Ángel; Piniella, J. F.

doi:10.1021/ja00084a069

Cited by 104 publications

(32 citation statements)

References 0 publications

Supporting

Mentioning

Contrasting

Unclassified

Order By: Relevance

“…20). 88 Reaction of this complex with norbornene or norbornadiene gave mixtures of isomers with high diastereomeric ratios. Compound 108 was subsequently utilized in the asymmetric synthesis of the angular triquinane derivatives 110 and 111 with 9.5: 1 and 12: 1 selectivities re~pectively.8~ The sulfur atom was proposed …”

Section: Fig 19 Chiral Auxiliary Mediated Intermolecular Pauson-khanmentioning

confidence: 99%

The Asymmetric Pauson-Khand Reaction. A Review

Ingate

Marco-Contellers

1998

Organic Preparations and Procedures International

109

View full text Add to dashboard Cite

Section: Fig 19 Chiral Auxiliary Mediated Intermolecular Pauson-khanmentioning

confidence: 99%

The Asymmetric Pauson-Khand Reaction. A Review

Ingate

Marco-Contellers

1998

Organic Preparations and Procedures International

109

View full text Add to dashboard Cite

“…Norbornene and related systems are commonly used in the intermolecular Pauson–Khand reaction. Since the early reports of Pauson and co‐workers,23a–c in which they showed norbornenes to be the most successful alkene partners, there have been many examples of their use in the presence of different metals and under different reaction conditions,15b–f, 30c, f, 32b, g, 40, 68a in the asymmetric version of the reaction,28e,h, 32d, i, 41 and in heterogeneous systems 30g–i. 42 Related systems such as 8‐oxabicyclo[3.2.1]octenes28b, 43 and heteroatom‐containing bicyclo[2.2.1]heptenes,28f, 40b, p, 42a, 43c, 44, 45 reveal similar or slightly lower levels of reactivity.…”

Section: Reactive Alkene Partners: the Lumo Energymentioning

confidence: 99%

The Intermolecular Pauson–Khand Reaction

2005

View full text Add to dashboard Cite

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.

show abstract

“…The Pauson–Khand reaction (PKR), which allows for the convergent assembly of cyclopentenones from an alkene and an acetylene‐dicobalt hexacarbonyl complex, has become a well‐established synthetic method . The successful participation of norbornadiene in the intermolecular Pauson–Khand reaction has been reported by Bernardes and Greene . The alkoxyethyne‐dicobalt hexacarbonyl complex derived from 10‐(methylthio)isoborneol, which could be converted to an unstable, sulfur‐chelated dicobalt pentacarbonyl complex, reacted with norbornadiene at low temperature to give the corresponding cyclopentenones in good yields with up to 92% diastereomeric excess.…”

Section: Pauson–khand Reactions Of Norbornadienes With Alkynesmentioning

confidence: 99%