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底物控制的一锅法合成:手性苯并二氢吡喃-2-酮及多环衍生物的合成途径

Substrate-Controlled, One-Pot Synthesis: Access to Chiral Chroman-2-one and Polycyclic Derivatives.

作者信息

Sun Xue-Li, Chen Ying-Han, Zhu Dan-Yang, Zhang Yan, Liu Yan-Kai

机构信息

Key Laboratory of Marine Drugs, Chinese Ministry of Education, School of Medicine and Pharmacy, Ocean University of China , Qingdao 266003, P. R. China.

Hubei Key Laboratory for Processing and Application of Catalytic Materials, Huanggang Normal University , Huanggang 438000, P. R. China.

出版信息

Org Lett. 2016 Feb 19;18(4):864-7. doi: 10.1021/acs.orglett.6b00160. Epub 2016 Feb 4.

Abstract

Based on the appropriate choice of electrophiles, one-pot, multicomponent, enantioselective domino reactions have been realized which contain a five-step sequence and provide highly efficient access to potentially bioactive chroman-2-one derivatives as a single diastereoisomer with excellent enantioselectivities and in high yields. This new strategy could significantly improve the previous protocol by directly starting from commercial 2-hydroxybenzaldehydes rather than preformed lactols, which have to be synthesized in several additional steps.

摘要

基于亲电试剂的恰当选择,实现了一锅多组分对映选择性多米诺反应,该反应包含五步序列,能够高效地得到潜在具有生物活性的色满-2-酮衍生物,以单一非对映异构体形式存在,具有优异的对映选择性且产率高。这一新策略通过直接从市售的2-羟基苯甲醛开始,而非从需额外几步合成的预制内酯出发,可显著改进先前的方案。

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