新型手性钳形PNN类配体在钯催化不对称烯丙基烷基化反应中的应用

doi:10.6023/cjoc202005090

有机化学 ›› 2020, Vol. 40 ›› Issue (10): 3362-3370.DOI: 10.6023/cjoc202005090 上一篇下一篇

所属专题：黄乃正院士七十华诞专辑

研究论文

新型手性钳形PNN类配体在钯催化不对称烯丙基烷基化反应中的应用

吴敦奇, 成轩, 刘炎开, 成果, 管笑宇, 邓清海

上海师范大学教育部资源化学重点实验室和上海市稀土功能材料重点实验室上海 200234

收稿日期:2020-05-30 修回日期:2020-06-16 发布日期:2020-07-09
通讯作者: 邓清海 E-mail:qinghaideng@shnu.edu.cn
基金资助:
国家自然科学基金（Nos.21402119，21772122）和上海绿色能源化工工程技术研究中心（No.18DZ2254200）资助项目.

A New Class of Chiral Pincer-Type PNN Ligands for Pd-Catalyzed Asymmetric Allylic Alkylation

Wu Dunqi, Cheng Xuan, Liu Yankai, Cheng Guo, Guan Xiaoyu, Deng Qinghai

The Education Ministry Key Lab of Resource Chemistry and Shanghai Key Laboratory of Rare Earth Functional Materials, Shanghai Normal University, Shanghai 200234

Received:2020-05-30 Revised:2020-06-16 Published:2020-07-09
Supported by:
Project supported by the National Natural Science Foundation of China (Nos. 21402119, 21772122) and the Shanghai Engineering Research Center of Green Energy Chemical Engineering (No. 18DZ2254200).

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摘要/Abstract

从便宜、易得的手性氨基酸出发通过5至6步反应制备了一种新型手性钳形PNN类配体oxpma.该类手性配体含有2至3个手性中心.将其用于钯催化的烯丙基酯的不对称烯丙基烷基化反应，能够以高的对映选择性（最高可达96%）获得相应的手性目标产物.

关键词: PNN配体, 钳形配体, 不对称催化, 不对称烯丙基烷基化反应

tridentate P,N,N-donor pincer ligands bearing two or three stereocenters, 1-(4,5-dihydro-oxazol-2-yl)-N-(2-(diphenylphosphanyl)benzyl)methanamines (oxpma), were synthesized starting from readily available amino acids in five or six steps. They were applied in palladium-catalyzed asymmetric allylic alkylation of allylic acetates to afford the desired products with high enantioselectivities (up to 96% ee).

Key words: PNN ligand, pincer ligand, asymmetric catalysis, asymmetric allylic alkylation

引用此文

吴敦奇, 成轩, 刘炎开, 成果, 管笑宇, 邓清海. 新型手性钳形PNN类配体在钯催化不对称烯丙基烷基化反应中的应用[J]. 有机化学, 2020, 40(10): 3362-3370.

Wu Dunqi, Cheng Xuan, Liu Yankai, Cheng Guo, Guan Xiaoyu, Deng Qinghai. A New Class of Chiral Pincer-Type PNN Ligands for Pd-Catalyzed Asymmetric Allylic Alkylation[J]. Chinese Journal of Organic Chemistry, 2020, 40(10): 3362-3370.

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新型手性钳形PNN类配体在钯催化不对称烯丙基烷基化反应中的应用

A New Class of Chiral Pincer-Type PNN Ligands for Pd-Catalyzed Asymmetric Allylic Alkylation

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