Diametric Stereocontrol in Dynamic Catalytic Reduction of Racemic Acyl Phosphonates: Divergence from α‑Keto Ester Congeners

An unexpected dichotomy was observed in the Ru-catalyzed asymmetric transfer hydrogenation of acyl phosphonates: reduction proceeded from the opposite face relative to that observed in the analogous reduction of α-keto esters. The first highly selective catalytic hydrogenation of acyl phosphonates w...

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Bibliographic Details
Published inJournal of the American Chemical Society Vol. 135; no. 2; pp. 594 - 597
Main Authors Corbett, Michael T, Johnson, Jeffrey S
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 16.01.2013
Amer Chemical Soc
Subjects
Acylation
Catalysis
Chemistry
Chemistry, Multidisciplinary
Esters - chemistry
Ketones - chemistry
Ligands
Molecular Structure
Organophosphonates - chemistry
Oxidation-Reduction
Physical Sciences
Ruthenium - chemistry
Science & Technology
Stereoisomerism
PHOSPHORUS
ASYMMETRIC TRANSFER HYDROGENATION
PHOSPHINIC ACID ANALOGS
KINETIC RESOLUTION
HETERO-DIELS-ALDER
ALDEHYDES
INHIBITORS
AL(SALALEN) COMPLEX
HIGHLY ENANTIOSELECTIVE HYDROPHOSPHONYLATION
HYDROXY PHOSPHONATES
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Summary:An unexpected dichotomy was observed in the Ru-catalyzed asymmetric transfer hydrogenation of acyl phosphonates: reduction proceeded from the opposite face relative to that observed in the analogous reduction of α-keto esters. The first highly selective catalytic hydrogenation of acyl phosphonates was utilized in the dynamic kinetic resolution of α-aryl acyl phosphonates, providing β-stereogenic α-hydroxy phosphonic acid derivatives.
Bibliography:NIH RePORTER
ObjectType-Article-1
SourceType-Scholarly Journals-1
ObjectType-Feature-2
content type line 23
ISSN:0002-7863
1520-5126
DOI:10.1021/ja310980q