Journal
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
Volume 139, Issue 28, Pages 9519-9522Publisher
AMER CHEMICAL SOC
DOI: 10.1021/jacs.7b05880
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Funding
- ERC [670668]
- EPSRC [EP/I038071/1]
- Austrian Science Fund (FWF) [J3919-N28]
- Swiss National Science Foundation [P2EZP2_165268]
- EPSRC [EP/I038071/1, EP/K03927X/1, EP/L011999/1] Funding Source: UKRI
- Swiss National Science Foundation (SNF) [P2EZP2_165268] Funding Source: Swiss National Science Foundation (SNF)
- Austrian Science Fund (FWF) [J 3919] Funding Source: researchfish
- Engineering and Physical Sciences Research Council [EP/L011999/1, EP/K03927X/1, EP/I038071/1] Funding Source: researchfish
- European Research Council (ERC) [670668] Funding Source: European Research Council (ERC)
- Austrian Science Fund (FWF) [J3919] Funding Source: Austrian Science Fund (FWF)
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Coupling reactions between benzylamines and boronic esters have been investigated. ortho-Lithiated benzylamines react with boronic esters and a N-activator to afford ortho-substituted benzylic boronic esters with formal 1,1'-benzylidene insertion into the C-B bond. The reaction occurs by a S(N)2' elimination and 1,2-metalate rearrangement of the N-activated boronate complex to afford a dearomatized intermediate, which undergoes a Lewis-acid catalyzed 1,3-borotropic shift to afford the boronic ester products in high yield and with excellent enantiospecificity. The use of enantioenriched alpha-substituted benzylamines gave the corresponding secondary boronic esters with high ee.
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