Regio- and Diastereoselective Radical Hydroboration of N-Aryl Enamine Carboxylates for the Synthesis of anti-?-Amino Organoborons

The regio-and diastereoselective hydroboration of N-aryl enamine carboxylates was achieved by dichloro-substituted N-heterocyclic carbene (NHC)-boryl radical to access the valuable anti-fi-amino boron skeleton. Excellent diastereoselectivity (>95:5 dr) was obtained using dichloro-NHC-BH3 (boryl r...

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Bibliographic Details
Published inOrganic letters Vol. 25; no. 16; pp. 2852 - 2856
Main Authors Zhao, Jinjin, Phang, Yeelin, Wang, Zhijuan, Dagnaw, Fentahun Wondu, Lu, Yi-Hong, Wang, Yi-Feng, Jin, Ji-Kang
Format Journal Article
LanguageEnglish
Published WASHINGTON Amer Chemical Soc 28.04.2023
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
ACID-DERIVATIVES
COPPER-CATALYZED AMINOBORATION
ESTERS
ENANTIOSELECTIVE ADDITION
POLARITY-REVERSAL CATALYSIS
1,1-DIBORYLALKANES
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Summary:The regio-and diastereoselective hydroboration of N-aryl enamine carboxylates was achieved by dichloro-substituted N-heterocyclic carbene (NHC)-boryl radical to access the valuable anti-fi-amino boron skeleton. Excellent diastereoselectivity (>95:5 dr) was obtained using dichloro-NHC-BH3 (boryl radical precursor) and the thiol catalyst. Broad substrate scope and good functional group tolerance were demonstrated. Further trans -formation of the product to amino alcohol exemplified the synthetic utility of this reaction.
ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.3c00818