Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 56, Issue 38, Pages 11584-11588Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201705829
Keywords
amines; boron; copper; diastereoselectivity; enantioselectivity
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Funding
- Basic Science Research Program through the National Research Foundation of Korea (NRF)
- Ministry of Science, ICT & Future Planning [NRF-2015R1C1A1A02036326]
- National Research Foundation of Korea [2015R1C1A1A02036326] Funding Source: Korea Institute of Science & Technology Information (KISTI), National Science & Technology Information Service (NTIS)
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Reported herein is an efficient copper(I)-catalytic system for the diastereo- and enantioselective 1,2-addition of 1,1-bis[(pinacolato)boryl]alkanes to protected imines to afford synthetically valuable enantioenriched beta-aminoboron compounds bearing contiguous stereogenic centers. The reaction exhibits a broad scope with respect to protected imines and 1,1bis[(pinacolato)boryl]alkanes, thus providing b-aminoboronate esters with excellent diastereo- and enantioselectivity. The synthetic utility of the obtained beta-aminoboronate ester was also demonstrated.
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