Rhodium-Catalyzed Asymmetric Addition of Potassium Organotrifluoroborates to N-Sulfonyl Ketimines

A rhodium-catalyzed asymmetric addition of readily available potassium organotrifluoroborates to both N-tosyl and N-nosyl ketimines has been developed. High enantioselectivity has been achieved by using a chiral diene ligand, and the nosyl group of the addition products can be easily removed while r...

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Published inOrganic letters Vol. 13; no. 12; pp. 2977 - 2979
Main Authors Shintani, Ryo, Takeda, Momotaro, Soh, Ying-Teck, Ito, Tomoaki, Hayashi, Tamio
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 17.06.2011
Amer Chemical Soc
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
MANNICH REACTION
TOSYLARYLIMINES
KETONES
REAGENTS
CHIRAL DIENE LIGANDS
IMINES
ARYLATION
NUCLEOPHILIC-ADDITION
QUATERNARY CARBON CENTERS
ENANTIOSELECTIVE STRECKER REACTION
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Summary:A rhodium-catalyzed asymmetric addition of readily available potassium organotrifluoroborates to both N-tosyl and N-nosyl ketimines has been developed. High enantioselectivity has been achieved by using a chiral diene ligand, and the nosyl group of the addition products can be easily removed while retaining the enantiomeric purity.
Bibliography:KAKEN
ObjectType-Article-1
SourceType-Scholarly Journals-1
ObjectType-Feature-2
content type line 23
ISSN:1523-7060
1523-7052
DOI:10.1021/ol200958q