Journal of Organic Chemistry
Journal of Organic Chemistry
4 years ago

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

Cinchona Alkaloid Catalyzed Enantioselective [4 + 2] Annulation of Allenic Esters and in Situ Generated ortho-Quinone Methides: Asymmetric Synthesis of Functionalized Chromans
Xu Yan, Liang-Liang Yang, Xiang-Zhi Zhang, Hanmin Huang, Yu-Hua Deng, Wen-Dao Chu, Ke-Yin Yu, Chun-An Fan
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).

Publisher URL: http://dx.doi.org/10.1021/acs.joc.7b00370

DOI: 10.1021/acs.joc.7b00370

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