Regioselective Hydroformylation of Allylic Alcohols

A highly regioselective hydroformylation of allylic alcohols is reported toward the synthesis of β-hydroxy-acid and aldehyde products. The selectivity is achieved through the use of a ligand that reversibly binds to alcohols in situ, allowing for a directed hydroformylation to occur. The application...

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Bibliographic Details
Published inOrganic letters Vol. 13; no. 10; pp. 2686 - 2689
Main Authors Lightburn, Thomas E, De Paolis, Omar A, Cheng, Ka H, Tan, Kian L
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 20.05.2011
Amer Chemical Soc
Subjects
Alcohols - chemical synthesis
Alcohols - chemistry
Aldehydes - chemical synthesis
Aldehydes - chemistry
Alkenes - chemistry
Catalysis
Chemistry
Chemistry, Organic
Combinatorial Chemistry Techniques
Molecular Structure
Physical Sciences
Propanols - chemistry
Science & Technology
Stereoisomerism
DIRECTING GROUP
ORGANIC-SYNTHESIS
ASYMMETRIC HYDROFORMYLATION
ENE CYCLIZATION PROCESS
RHODIUM-CATALYZED HYDROFORMYLATION
SCAFFOLDING LIGAND
PRACTICAL METHOD
DESYMMETRIZING HYDROFORMYLATION
ENANTIOSELECTIVE HYDROFORMYLATION
STEREOSELECTIVE HYDROFORMYLATION
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Summary:A highly regioselective hydroformylation of allylic alcohols is reported toward the synthesis of β-hydroxy-acid and aldehyde products. The selectivity is achieved through the use of a ligand that reversibly binds to alcohols in situ, allowing for a directed hydroformylation to occur. The application to trisubstituted olefins was also demonstrated, which yields a single diastereomer product consistent with a stereospecific addition of CO and hydrogen.
Bibliography:NIH RePORTER
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ISSN:1523-7060
1523-7052
DOI:10.1021/ol200782d