Novel Axially Chiral Phosphine Ligand with a Fluoro Alcohol Moiety for Rh-Catalyzed Asymmetric Arylation of Aromatic Aldehydes

A new chiral phosphine ligand (R)-1 possessing a fluoroalcohol moiety was prepared. The (R)-1-coordinated Rh(I) complex showed an excellent catalytic activity for asymmetric 1,2-addition of arylboronic acids to aldehydes to afford highly enantioenriched diarylmethanols. The fluoroalcohol moiety in l...

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Published inOrganic letters Vol. 12; no. 11; pp. 2520 - 2523
Main Authors Morikawa, Satoshi, Michigami, Kyosuke, Amii, Hideki
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 04.06.2010
Amer Chemical Soc
Subjects
Alcohols - chemistry
Aldehydes - chemistry
Catalysis
Chemistry
Chemistry, Organic
Hydrocarbons, Fluorinated - chemistry
Ligands
Molecular Structure
Phosphines - chemical synthesis
Phosphines - chemistry
Physical Sciences
Rhodium - chemistry
Science & Technology
Stereoisomerism
BORONIC ACIDS
HIGHLY ENANTIOSELECTIVE SYNTHESIS
KETONES
COMPLEX
HYDROGENATION
RHODIUM
ME-BIPAM
PHENYL TRANSFER
DIARYLMETHANOLS
ARYLBORONIC ACIDS
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Summary:A new chiral phosphine ligand (R)-1 possessing a fluoroalcohol moiety was prepared. The (R)-1-coordinated Rh(I) complex showed an excellent catalytic activity for asymmetric 1,2-addition of arylboronic acids to aldehydes to afford highly enantioenriched diarylmethanols. The fluoroalcohol moiety in ligand (R)-1 plays a pivotal role for the high enantioselectivity of the present Rh(I)-catalyzed transformation.
Bibliography:ObjectType-Article-1
SourceType-Scholarly Journals-1
ObjectType-Feature-2
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ISSN:1523-7060
1523-7052
DOI:10.1021/ol100697a