Asymmetric Catalytic Intramolecular Pauson–Khand Reactions with Ir(phox) Catalysts

Lu, Zhong‐Lin; Neumann, Eva; Pfaltz, Andreas

doi:10.1002/ejoc.200700330

Cited by 34 publications

(10 citation statements)

References 40 publications

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“…In the case of a related iridium complex bearing a chelating phosphanyl–oxazoline P,N‐ligand, the carbonylation product was stable enough to be characterized by X‐ray analysis. Unfortunately, no spectroscopic data were provided for this complex of general formula [(P,N)Ir(CO) 2 ] · PF 6 21…”

Section: Resultsmentioning

confidence: 99%

Structure–Activity Relationship in the Iridium‐Catalyzed Isomerization of Primary Allylic Alcohols

et al. 2012

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The evaluation of a series of cationic iridium complexes in the isomerization of primary allylic alcohols has revealed the unique ability of Crabtree catalysts [(Cy3P)(C6H5N)Ir(cod)]·X 1a (X = PF6) and 1b (X = BArF; cod = 1,5-cyclooctadiene) to catalyze efficiently this transformation. Emphasis has been placed on understanding the electronic factors that govern the catalytic process by using a range of para-substituted pyridine N-donor ligands. Excellent correlations between analytical data (13C NMR chemical shift; νCO) and established thermodynamic and kinetic parameters (pKa, Mayr nucleophilicity parameter N) have been elaborated. Overall, the results obtained point to the possibility of qualitatively predicting the activity of Crabtree catalyst analogues in the isomerization of primary allylic alcohols

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Section: Resultsmentioning

confidence: 99%

Structure–Activity Relationship in the Iridium‐Catalyzed Isomerization of Primary Allylic Alcohols

et al. 2012

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“…Recently, Pfaltz reported a chiral cationic Ir(phox) complex that was effective in asymmetric Pauson–Khand‐type reactions (Scheme ) 84. Under optimized reaction conditions, high yields and enantioselectivities of >90 % ee were obtained.…”

Section: Iridium‐catalysed Pauson–khand‐type Cyclizationsmentioning

confidence: 99%

A Decade of Advancements in Pauson–Khand‐Type Reactions

2010

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“…Lu et al have accomplished a highly enantioselective (up to 97% ee) preparation of 230 by using cationic iridium complexes ( S )- 234 derived from chiral phosphine-oxazoline ( S )- 233 (Scheme ). The nature of the anion was found to have a significant influence on both the enantioselectivity and the yield. The absolute configuration of cyclopentafuranone 230 (X = O) was determined as ( R ), while the others were not specified.…”

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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Asymmetric Catalytic Intramolecular Pauson–Khand Reactions with Ir(phox) Catalysts

Cited by 34 publications

References 40 publications

Structure–Activity Relationship in the Iridium‐Catalyzed Isomerization of Primary Allylic Alcohols

Structure–Activity Relationship in the Iridium‐Catalyzed Isomerization of Primary Allylic Alcohols

A Decade of Advancements in Pauson–Khand‐Type Reactions

Synthesis of Chiral Cyclopentenones

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