4.7 Article

Cinchona Alkaloid Catalyzed Enantioselective [4+2] Annulation of Allenic Esters and in Situ Generated ortho-Quinone Methides: Asymmetric Synthesis of Functionalized Chromans

Journal

JOURNAL OF ORGANIC CHEMISTRY
Volume 82, Issue 10, Pages 5433-5440

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/acs.joc.7b00370

Keywords

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Funding

  1. National Natural Science Foundation of China [21572083, 21322201, 21290180]
  2. Fundamental Research Funds for the Central Universities [lzujbky-2015-48, lzujbky-2016-ct02, lzujbky-2016-ct07]
  3. Program for Changjiang Scholars and Innovative Research Team in University [IRT_15R28]
  4. 111 Project of the Ministry of Education of the People's Republic of China [111-2-17]
  5. Chang Jiang Scholars Program

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A novel enantioselective [4 + 2] annulation of the allenoates having a unique positive ortho-effect with in situ generated ortho-quinone methides has been developed under the catalysis of Cinchona alkaloid. This chiral amine-catalyzed reaction provides an alternative route to asymmetric catalytic construction of synthetically interesting, highly functionalized chiral chromans in good to excellent enantioselectivities (up to 97% ee).

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