Journal
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
Volume 138, Issue 46, Pages 15146-15149Publisher
AMER CHEMICAL SOC
DOI: 10.1021/jacs.6b11229
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Funding
- National Research Foundation of Korea (NRF) [NRF-2016R1A2B4011719, NRF-2016R1A4A1011451]
- Korea government (MEST)
- National Research Foundation of Korea [2016R1A2B4011719, 2016R1A4A1011451] Funding Source: Korea Institute of Science & Technology Information (KISTI), National Science & Technology Information Service (NTIS)
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An efficient synthetic method for preparing enantioenriched secondary borylalkanes has been achieved through a copper-catalyzed regio- and enantioselective hydroallylation of alkenyl boronates and boramides employing hydrosilanes and allylic phosphates. In the presence of a copper catalyst with a chiral Walphos ligand, a range of alkenylboron compounds with an aryl, heteroaryl, or alkyl substituent produced secondary homoallylic alkylboron compounds in good yields and with high enantioselectivities up to 99% ee. The utility of the resulting alkylboronates was demonstrated in an efficient synthesis of (S)-massoialactone.
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