Enantioselective Rhodium-Catalyzed Arylation of Cyclic N‑Sulfamidate Alkylketimines: A New Access to Chiral β‑Alkyl-β-aryl Amino Alcohols

The enantioselective rhodium-catalyzed 1,2-addition of arylboronates to cyclic N-sulfamidate alkylketimines was developed. With a rhodium/diene complex as catalyst, high enantioselectivity and broad functional group tolerance were observed. The resulting sulfamidates can easily be converted into chi...

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Bibliographic Details
Published inOrganic letters Vol. 16; no. 12; pp. 3400 - 3403
Main Authors Chen, Ya-Jing, Chen, Ya-Heng, Feng, Chen-Guo, Lin, Guo-Qiang
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 20.06.2014
Amer Chemical Soc
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
ELECTROPHILIC DISPLACEMENT REACTIONS
ASYMMETRIC-SYNTHESIS
ARENEBORONIC ACIDS
ANTI-1,2-AMINO ALCOHOLS
STEERING LIGANDS
PROTECTED 1,2-AMINO ALCOHOLS
DIENE LIGANDS
CARBONYL-COMPOUNDS
NUCLEOPHILIC-ADDITION
ARYLBORONIC ACIDS
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Summary:The enantioselective rhodium-catalyzed 1,2-addition of arylboronates to cyclic N-sulfamidate alkylketimines was developed. With a rhodium/diene complex as catalyst, high enantioselectivity and broad functional group tolerance were observed. The resulting sulfamidates can easily be converted into chiral β-alkyl-β-aryl amino alcohols.
Bibliography:ObjectType-Article-1
SourceType-Scholarly Journals-1
ObjectType-Feature-2
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ISSN:1523-7060
1523-7052
DOI:10.1021/ol501464e