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Deng YH, Chu WD, Zhang XZ, et al. Cinchona Alkaloid Catalyzed Enantioselective [4 + 2] Annulation of Allenic Esters and in Situ Generated ortho-Quinone Methides: Asymmetric Synthesis of Functionalized Chromans. J Org Chem. 2017;82(10):5433-5440doi: 10.1021/acs.joc.7b00370.
Deng, Y. H., Chu, W. D., Zhang, X. Z., Yan, X., Yu, K. Y., Yang, L. L., Huang, H., & Fan, C. A. (2017). Cinchona Alkaloid Catalyzed Enantioselective [4 + 2] Annulation of Allenic Esters and in Situ Generated ortho-Quinone Methides: Asymmetric Synthesis of Functionalized Chromans. The Journal of organic chemistry, 82(10), 5433-5440. https://doi.org/10.1021/acs.joc.7b00370
Deng, Yu-Hua, et al. "Cinchona Alkaloid Catalyzed Enantioselective [4 + 2] Annulation of Allenic Esters and in Situ Generated ortho-Quinone Methides: Asymmetric Synthesis of Functionalized Chromans." The Journal of organic chemistry vol. 82,10 (2017): 5433-5440. doi: https://doi.org/10.1021/acs.joc.7b00370
Deng YH, Chu WD, Zhang XZ, Yan X, Yu KY, Yang LL, Huang H, Fan CA. Cinchona Alkaloid Catalyzed Enantioselective [4 + 2] Annulation of Allenic Esters and in Situ Generated ortho-Quinone Methides: Asymmetric Synthesis of Functionalized Chromans. J Org Chem. 2017 May 19;82(10):5433-5440. doi: 10.1021/acs.joc.7b00370. Epub 2017 May 01. PMID: 28421762.
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J Org Chem. 2017 May 19;82(10):5433-5440. doi: 10.1021/acs.joc.7b00370. Epub 2017 May 01.

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

The Journal of organic chemistry

Yu-Hua Deng, Wen-Dao Chu, Xiang-Zhi Zhang, Xu Yan, Ke-Yin Yu, Liang-Liang Yang, Hanmin Huang, Chun-An Fan

Affiliations

  1. State Key Laboratory for Oxo Synthesis and Selective Oxidation, Lanzhou Institute of Chemical Physics, Chinese Academy of Sciences , Lanzhou 730000, China.
  2. University of Chinese Academy of Sciences , Beijing 100049, China.
  3. State Key Laboratory of Applied Organic Chemistry, College of Chemistry and Chemical Engineering, Lanzhou University , 222 Tianshui Nanlu, Lanzhou 730000, China.
  4. Collaborative Innovation Center of Chemical Science and Engineering (Tianjin) , Tianjin 300071, China.

PMID: 28421762 DOI: 10.1021/acs.joc.7b00370

Abstract

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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