Journal
TETRAHEDRON
Volume 68, Issue 17, Pages 3444-3449Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tet.2011.07.061
Keywords
Boration; Conjugate reduction; Copper; Asymmetric synthesis; Vinylboronates
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Funding
- National Research Foundation [R01-2008-000-20332-0, NRF-20090085824, NRF-20110009533]
- National Research Foundation of Korea [R01-2008-000-20332-0] Funding Source: Korea Institute of Science & Technology Information (KISTI), National Science & Technology Information Service (NTIS)
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Phosphine copper(I) complexes efficiently catalyzed the mono-boration of electron-deficient alkynes in the presence of MeOH and also catalyzed conjugate reductions of alkenylboronates bearing an electron-withdrawing group. The mono-addition of bis(pinacolato)diboron to alkynes catalyzed by a copper-Xantphos complex produced vinylboronates with high regio and stereoselectivity and asymmetric reduction of the vinylboronates by a chiral copper bisphosphine catalyst allowed the synthesis of valuable chiral boranes with high enantioselectivity. One-pot boration/asymmetric reduction of alpha,beta-unsaturated allcynoates could be conducted with a single copper phosphine catalyst (C) 2011 Elsevier Ltd. All rights reserved.
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