Journal
CHEMISTRY-AN ASIAN JOURNAL
Volume 13, Issue 17, Pages 2365-2368Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/asia.201800121
Keywords
asymmetric catalysis; borylative coupling; copper; cyclization; indolines
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Funding
- National Research Foundation of Korea (NRF) - Korean government (MEST) [NRF-2016R1A2B4011719, NRF-2016R1A4A1011451]
- China Scholarship Council [201508260066]
- National Research Foundation of Korea [2016R1A2B4011719] Funding Source: Korea Institute of Science & Technology Information (KISTI), National Science & Technology Information Service (NTIS)
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A copper-catalyzed, intramolecular borylative cyclization of vinyl arenes with imines is reported, which affords enantio-enriched indolines as a single diastereomer under mild conditions. A benzylcopper species is generated by Cu-Bpin addition to the alkene, which then acts as a nucleophile for intramolecular imine addition. The reaction is applicable to various vinyl arenes with an imine moiety at the ortho-position, including heterocycles, for formation of borylated indolines in good yields and ee values up to 90%.
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