Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 57, Issue 39, Pages 12930-12934Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201805476
Keywords
allylic alkylation; enantioselectivity; homogeneous catalysis; organoboron compounds; zinc
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Funding
- Samsung Science and Technology Foundation [SSTF-BA1701-11]
- National Research Foundation of Korea (NRF) [NRF-2017H1A2A1045655, NRF-2016H1A2A1908616]
- POSCO Green Science Program
- Cheongam Science Fellowship
- National Research Foundation of Korea [2016H1A2A1908616, 2017H1A2A1045655] Funding Source: Korea Institute of Science & Technology Information (KISTI), National Science & Technology Information Service (NTIS)
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We report the successful generation of (diborylmethyl)zinc(II) species by transmetallation beteween isolable (diborylmethyl)lithium and zinc(II) halide (X=Br, Cl) and their application in the synthesis of enantioenriched gem-diborylalkanes bearing a stereogenic center at the beta-position of the diboryl groups by an asymmetric allylic substitution reaction. The reaction has a broad substrate scope, and various enantioenriched gem-diborylalkanes can be obtained in good yields with excellent enantioselectivity. Further elaboration of the enantioenriched gem-diborylalkanes provides access to a diverse set of valuable chiral building blocks.
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