Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 57, Issue 39, Pages 12935-12939Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201805705
Keywords
alkenes; asymmetric catalysis; cobalt; diborylation; homogeneous catalysis
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Funding
- Ministry of Education (MOE) of Singapore [R-143-000-A07-112]
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We report an asymmetric synthesis of enantioenriched gem-bis(boryl)alkanes in an enantioselective diborylation of 1,1-disubstituted alkenes catalyzed by Co(acac)(2)/(R)-DM-segphos. A range of activated and unactivated alkenes underwent this asymmetric diborylation in the presence of cyclooctene as a hydrogen acceptor, affording the corresponding gem-bis(boryl)alkanes with high enantioselectivity. The synthetic utility of these chiral organoboronate compounds was demonstrated through several stereospecific derivatizations and the synthesis of sesquiterpene and sesquiterpenoid natural products.
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