Efficient Synthesis of Chiral Drugs Facilated by P-Chiral Phosphorus Ligands

doi:10.6023/cjoc202003015

Chinese Journal of Organic Chemistry ›› 2020, Vol. 40 ›› Issue (6): 1409-1422.DOI: 10.6023/cjoc202003015 Previous Articles Next Articles

ACCOUNT

P-手性膦配体促进的手性药物高效合成

许容华^a, 杨贺^c, 汤文军^a,b,d

a 上海科技大学物质科学与技术学院上海 201210;
b 中国科学院上海有机化学研究所生命有机化学国家重点实验室上海 200032;
c 南方科技大学深圳格拉布斯研究院广东深圳 518055;
d 国科大杭州高等研究院化学和材料科学学院杭州 310024

收稿日期:2020-03-06 修回日期:2020-04-06 发布日期:2020-04-17
通讯作者: 杨贺, 汤文军 E-mail:yanghe@sioc.ac.cn;tangwenjun@sioc.ac.cn
基金资助:
国家自然科学基金（No.21725205，21432007，21572246）、中国科学院战略性先导科技专项（XDB20000000）和王宽诚教育基金会资助项目.

Efficient Synthesis of Chiral Drugs Facilated by P-Chiral Phosphorus Ligands

Xu Ronghua^a, Yang He^c, Tang Wenjun^a,b,d

a School of Physical Science and Technology, ShanghaiTech University, Shanghai 201210;
b State Key Laboratory of Bio-Organic and Natural Products Chemistry, Center for Excellence in Molecular Synthesis, Shanghai Institute of Organic Chemistry, Chinese Academy of Science, Shanghai 200032;
c Shenzhen Grubbs Institute, Southern University of Science and Technology, Shenzhen, Guangdong 518055;
d School of Chemistry and Material Sciences, Hangzhou Institute for Advanced Study, University of Chinese Academy of Sciences, Hangzhou 310024

Received:2020-03-06 Revised:2020-04-06 Published:2020-04-17
Supported by:
Project supported by the National Natural Science Foundation of China (Nos. 21725205, 21432007, 21572246), the Strategic Priority Research Program of the Chinese Academy of Sciences (XDB20000000) and the K. C. Wong Education Foundation.

Development of efficient and practical asymmetric catalytic reactions plays a pivotal role for the concise syntheses of chiral drugs. Chiral ligands and catalysts are crucial for the selectivity and reactivity of the catalytic reactions. In this account, the design and development of a series of P-chiral mono- and bis-phosphorus ligands were summarized based on a benzooxaphosphane backbone and their applications in the synthesis of chiral drugs. Beside their P-chirality, these ligands are structurally rigid, sterically bulky, and electron-rich, providing good physical properties and tunabilities. Facilitated by these chiral ligands, a series of efficient and practical reactions including asymmetric hydrogenation, asymmetric cross-coupling, asymmetric cyclization, and asymmetric nucleophilic additions have been developed. The excellent conversions, yields, regioselectivities, enantioselectivities, and broad substrate scope have enabled concise and efficient syntheses of a series of chiral drugs.

Key words: chiral phosphorus ligands, transition metal catalysis, asymmetric synthesis, enantioselectivity, chiral drugs

Cite this article

Xu Ronghua, Yang He, Tang Wenjun. Efficient Synthesis of Chiral Drugs Facilated by P-Chiral Phosphorus Ligands[J]. Chinese Journal of Organic Chemistry, 2020, 40(6): 1409-1422.

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P-手性膦配体促进的手性药物高效合成

Efficient Synthesis of Chiral Drugs Facilated by P-Chiral Phosphorus Ligands

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