Journal
CHEMISTRY-A EUROPEAN JOURNAL
Volume 15, Issue 8, Pages 1939-1943Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.200802150
Keywords
asymmetric catalysis; boron; conjugate addition; copper; enones
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Funding
- Korea Research Foundation grant [KRF2007-531-C00034]
- Korea Science and Engineering Foundation grant [R01-2008-000-20332-0]
- Korean Government
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The enantioselective beta-boration of various acyclic enones has been studied by using chiral diphosphine-copper complexes. Good to excellent yields and enantioselectivities (up to 97% ee (enantiomeric excess)) were observed for a range of substrates under optimized conditions. In this transformation, the addition of a controlled amount of alcohol, especially methyl alcohol, is critical to obtain products in high ee and yield. This methodology accommodates structural variation of acyclic enones and provides access to a range of functionalized chiral organoboronates in high enantiomeric purity.
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