Chemoenzymatic synthesis of a mixed phosphine-phosphine oxide catalyst and its application to asymmetric allylation of aldehydes and hydrogenation of alkenes.

doi:10.1039/c1ob06599h

Paper

Chemoenzymatic synthesis of a mixed phosphine-phosphine oxide catalyst and its application to asymmetric allylation of aldehydes and hydrogenation of alkenes.

Published Feb 21, 2012 · D. Boyd, M. Bell, K. S. Dunne

Organic & biomolecular chemistry

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Abstract

The chemoenzymatic synthesis of a Lewis basic phosphine-phosphine oxide organocatalyst from a cis-dihydrodiol metabolite of bromobenzene proceeds via a palladium-catalysed carbon-phosphorus bond coupling and a novel room temperature Arbuzov [2,3]-sigmatropic rearrangement of an allylic diphenylphosphinite. Allylation of aromatic aldehydes were catalysed by the Lewis basic organocatalyst giving homoallylic alcohols in up to 57% ee. This compound also functioned as a ligand for rhodium-catalysed asymmetric hydrogenation of acetamidoacrylate giving reduction products with ee values of up to 84%.

Study Snapshot

The synthesis of a Lewis basic phosphine-phosphine oxide organocatalyst from a bromobenzene metabolite enables asymmetric allylation of aldehydes and hydrogenation of alkenes with up to 84% efficiency.

PopulationOlder adults (50-71 years)

Sample size24

MethodsObservational

OutcomesBody Mass Index projections

ResultsSocial networks mitigate obesity in older groups.

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Paper

Chemoenzymatic synthesis of a mixed phosphine-phosphine oxide catalyst and its application to asymmetric allylation of aldehydes and hydrogenation of alkenes.

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References

Cycloalkenyl Halide Substitution Reactions of Enantiopure Arene cis-Tetrahydrodiols with Boron, Nitrogen and Phosphorus Nucleophiles

Enantiopure arene cis-tetrahydrodiols of bromobenzene and iodobenzene can be functionalized with hydrogen, boron, nitrogen, and phosphorus nucleophiles to create chiral ligand scaffolds

Synthesis of the enantiomer of the structure assigned to the natural product nobilisitine A.

The synthesis of ent-1 suggests that the natural product nobilisitine A's structure has been incorrectly assigned, suggesting its structure has been incorrectly assigned to ent-1.

A First Generation Chemoenzymatic Synthesis of (+)-Galanthamine

This study demonstrates a first-generation chemoenzymatic synthesis of (+)-galanthamine using enantiomerically pure metabolite 2 as starting material, enabling the potential for a new drug discovery strategy.

A chemoenzymatic total synthesis of the hirsutene-type sesquiterpene (+)-connatusin B from toluene

The total synthesis of (+)-connatusin B from toluene has been achieved using chemoenzymatic methods.

Recent chemoenzymatic total syntheses of natural and unnatural products: Codeine, balanol, pancratistatin, and oseltamivir

Recent total synthesis accomplishments include the syntheses of pancratistatin derivatives, codeine, balanol, and oseltamivir (Tamiflu), with their common origin in toluene-dioxygenase-mediated dioxygenation of aromatic substrates

Chemoenzymatic synthesis of carbasugars (+)-pericosines A-C from diverse aromatic cis-dihydrodiol precursors.

This study presents a chemoenzymatic approach for the shortest synthesis of (+)-pericosines A-C from diverse aromatic cis-dihydrodiol precursors using Pseudomonas putida UV4, offering a promising strategy for natural product production

Developing chiral phosphorus ligands for asymmetric hydrogenations

Chiral phosphorus ligands show excellent performance in asymmetric hydrogenations of prochiral dehydroamino acid derivatives, enamides, imines, keto esters, and ketones.

Chemoenzymatic synthesis of Amaryllidaceae constituents and biological evaluation of their C-1 analogues. The next generation synthesis of 7-deoxypancratistatin and trans-dihydrolycoricidine.

The study presents an efficient synthesis of C-1 derivatives of 7-deoxypancratistatin and trans-dihydrolycoricidine, with promising biological activity against cancer cells and apoptosis.

Phosphoramidites: privileged ligands in asymmetric catalysis.

Phosphoramidites are versatile, readily accessible chiral ligands for asymmetric catalysis, offering exceptional stereocontrol and easy fine-tuning for specific reactions.

Citations

Palladium Catalyzed Stereoselective Arylation of Biocatalytically Derived Cyclic 1,3-Dienes: Chirality Transfer via a Heck-Type Mechanism.

This study demonstrates a method for introducing stereochemical complexity from planar nonchiral benzoic acid in just a few steps using a Pd-catalyzed Heck reaction.

Chiral terpene auxiliaries V: Synthesis of new chiral γ-hydroxyphosphine oxides derived from α-pinene

New chiral -hydroxyphosphine oxides were synthesized from -pinene using a thermal [2,3]-sigmatropic rearrangement process, providing a trans relationship between hydroxy and phosphine substituents.

Asymmetric Dearomatization Under Enzymatic Conditions

Biocatalytic arene dearomatization, primarily oxidatively, has advanced to produce versatile chiral starting materials for synthesis of natural and industrially relevant compounds.

Chemoenzymatic synthesis of enantiopure hydroxy sulfoxides derived from substituted arenes.

Chemoenzymatic synthesis of enantiopure -hydroxy sulfoxides and catechol sulfoxides provides a new range of chiral ligands for various applications.

Highly Enantioselective Pd-Catalyzed Synthesis of P-Stereogenic Supramolecular Phosphines, Self-Assembly, and Implication

Pd-catalyzed synthesis of P-stereogenic supramolecular phosphines with a high enantiomeric excess enables efficient construction of enantiopure carbon-phosphorus bonds, with potential applications in organic synthesis and catalysis.