Chiral Resolution of Biphenol and Asymmetric Alkylation under Phase Transfer Catalysis

doi:10.6023/cjoc202003028

Chinese Journal of Organic Chemistry ›› 2020, Vol. 40 ›› Issue (7): 1955-1966.DOI: 10.6023/cjoc202003028 Previous Articles Next Articles

联苯二酚的手性拆分及相转移催化不对称烷基化研究

柯翠连^a, 徐伟平^a, 刘达^a, 刘艳^a, Keiji Maruoka^a,b

a 广东工业大学轻工化工学院广州 510006;
b Graduate School of Pharmaceutical Sciences, Kyoto University, Sakyo, Kyoto, 606-8501, Japan

收稿日期:2020-03-11 修回日期:2020-04-28 发布日期:2020-05-11
通讯作者: 刘艳, Keiji Maruoka E-mail:yanliu@gdut.edu.cn;maruoka@kuchem.kyoto-u.ac.jp
基金资助:
国家自然科学基金（Nos.21977019，21502023）、广东省重点领域研发计划（No.2019B020201005）、广东省新药筛选重点实验室开放课题（No.GDKLNDS-2018OF004）.

Chiral Resolution of Biphenol and Asymmetric Alkylation under Phase Transfer Catalysis

Ke Cuilian^a, Xu Weiping^a, Liu Da^a, Liu Yan^a, Maruoka Keiji^a,b

a School of Chemical Engineering and Light Industry, Guangdong University of Technology, Guangzhou 510006, China;
b Graduate School of Pharmaceutical Sciences, Kyoto University, Sakyo, Kyoto, 606-8501, Japan

Received:2020-03-11 Revised:2020-04-28 Published:2020-05-11
Supported by:
Project supported by the National Natural Science Foundation of China (Nos. 21977019, 21502023), the Guangdong Provincial Key Research and Development Program (No. 2019B020201005), the Open Project of Guangdong Provincial Key Laboratory of New Drug Screening (No. GDKLNDS-2018OF004).

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Abstract

Chiral phase transfer catalysts play extrememly important role in the construction of natural products, the core structures of chiral drugs, and functional chiral chemicals, therefore have attracted more and more attention in recent years. In this paper, the chiral resolution of biphenyl skeletons was achieved by utilizing the readily available (R)-α-methoxy benzene acetic acid as resolution agent. A series of new biphenyl type of phase transfer catalysts were designed and synthesized based on the optically pure C₂-symmetric chiral biphenyl framework. These catalysts are readily applicable to asymmetric alkylation of N-(diphenylmethylene)glycine tert-butyl ester with excellent enantioselectivity (up to 96%) and yield (up to 97%). The structure-activity relationship study on these catalysts showed that the methylation of hydroxyl group at C2 and C2' position is favorable for the selectivity, introduction of tert-butyl group at C3 and C3' position is unfavorable to both selectivity and reactivity. The catalysts bearing 3,4,5-trifluorophenyl group or 3,5-bis(trifluoromethyl)phenyl group at C5 and C5' position showed good reactivity and selectivity.

Key words: phase-transfer catalysis, biphenyl derivatives, chiral resolution, asymmetric alkylation

Cite this article

Ke Cuilian, Xu Weiping, Liu Da, Liu Yan, Maruoka Keiji. Chiral Resolution of Biphenol and Asymmetric Alkylation under Phase Transfer Catalysis[J]. Chinese Journal of Organic Chemistry, 2020, 40(7): 1955-1966.

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联苯二酚的手性拆分及相转移催化不对称烷基化研究

Chiral Resolution of Biphenol and Asymmetric Alkylation under Phase Transfer Catalysis

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