On the asymmetric rh(I) catalyzed [4+2] cycloisomerization reaction. Electronic and torsional ligand control of absolute stereoselection.

McKinstry, Lydia; Livinghouse, Tom

doi:10.1016/s0040-4020(01)80636-0

Cited by 111 publications

(44 citation statements)

References 19 publications

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“…Although there are several examples of Rh(I)-catalyzed [4+2] cycloaddition of diene with alkene, [35][36][37][38][39][40][41][42] cycloisomerization between a diene and alkene catalyzed by Rh(I) complex is still not available in the literature. Thus, this cycloisomerization of various substrates was examined (Table 3).…”

Section: 29)mentioning

confidence: 99%

Development of Novel Cyclizations <i>via</i> Rhodacycle Intermediate and Its Application to Synthetic Organic Chemistry

Oonishi

2015

Chem. Pharm. Bull.

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Novel Rh(I)-catalyzed cyclizations through a different type of rhodacycle intermediate which is formedby hydroacylation of 4,6-dienal or oxidative addition of diene and alkene are described. Hydroacylation of 4,6-dienal afforded various 7-membered rings in good to high yields, while cycloisomerization of diene and alkene provided 5-or 6-membered rings in good yields. On the basis of these studies, we have also succeeded in developing the sequential reaction of hydroacylation followed by cycloisomerization to produce bicyclic compounds in a stereoselective manner and thus this reaction was expanded to the synthesis of epiglobulol. Furthermore, both Rh(I)-catalyzed hydroacylation and cycloisomerization using ionic liquid (IL) as a solvent were investigated and it was found that the IL recovered after the reaction, which contains the Rh(I) catalyst, could be recycled several times without loss of catalytic activity.

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Section: 29)mentioning

confidence: 99%

Development of Novel Cyclizations <i>via</i> Rhodacycle Intermediate and Its Application to Synthetic Organic Chemistry

Oonishi

2015

Chem. Pharm. Bull.

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“…[13] The phosphorus-boron bond of 48 was cleaved by conventional methods [54,55] to leave the free (S,S)-diphosphines in almost quantitative yields. Precatalysts 50 were obtained from the immediate complexation of free phosphines 3 and [Rh(nbd) 2 ]BF 4 .…”

Section: Bisp* and Miniphos: Synthesis And Characteristic Featuresmentioning

confidence: 99%

Recent Developments in Catalytic Asymmetric Hydrogenation Employing P‐Chirogenic Diphosphine Ligands

2003

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Rhodium‐ and ruthenium‐catalyzed asymmetric hydrogenations reactions employing C2‐symmetric chiral diphosphine ligands have a long history, and exceedingly high enantioselectivities have been reported. On the other hand, metal complexes containing P‐chirogenic, electron‐rich diphosphine ligands such as 1,2‐bis(alkylmethylphosphino)ethane (BisP*) and bis(alkylmethylphosphino)methane (MiniPHOS) have been tested only recently, and proved greatly successful. These results prompted intensive research amongst organic chemists, and the scope and limitations of the use of ligands bearing the chiral center at phosphorus atoms is presented in this review. The most recent data have been collected and summarized. In terms of ligand design, it is necessary to address an important question: “which properties are responsible for very high enantioselectivity in hydrogenation reactions?”. To this extent, a full discussion of new aspects on the mechanism, in particular the demonstration of a dihydride mechanism for enantioselective hydrogenation as opposed to the unsaturated mechanism widely accepted so far, also constitutes an important part of this review.

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“…We 66 and others 67 extended this method to alkenes and allenes and to other metal catalysts. The allenes proved especially interesting as they work well with 5-, 6-, and 7-atom tethers giving rise to 5-6, 6-6, and 6-7 bicycles, common to a variety of important targets.…”

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confidence: 99%

Toward the ideal synthesis and transformative therapies: the roles of step economy and function oriented synthesis

Wender

2013

Tetrahedron

103

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On the asymmetric rh(I) catalyzed [4+2] cycloisomerization reaction. Electronic and torsional ligand control of absolute stereoselection.

Cited by 111 publications

References 19 publications

Development of Novel Cyclizations <i>via</i> Rhodacycle Intermediate and Its Application to Synthetic Organic Chemistry

Development of Novel Cyclizations <i>via</i> Rhodacycle Intermediate and Its Application to Synthetic Organic Chemistry

Recent Developments in Catalytic Asymmetric Hydrogenation Employing P‐Chirogenic Diphosphine Ligands

Toward the ideal synthesis and transformative therapies: the roles of step economy and function oriented synthesis

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