Asymmetric synthesis of 1,2-amino alcohols using (S)-indoline chiral auxiliary

Youn, So Won; Choi, Jun Young; Kim, Yong Hae

doi:10.1002/(sici)1520-636x(2000)12:5/6<404::aid-chir19>3.0.co;2-2

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Copper‐Catalyzed Asymmetric Synthesis of Borylated cis‐Disubstituted Indolines

Kim

Yang

et al. 2018

Chemistry An Asian Journal

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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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