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2020 , Vol. 40 >Issue 10: 3362 - 3370

DOI: https://doi.org/10.6023/cjoc202005090

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
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  • 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

  网络出版日期: 2020-07-09

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.

收起

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

Received date: 2020-05-30

  Revised date: 2020-06-16

  Online 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

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

本文引用格式

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 . DOI: 10.6023/cjoc202005090

Abstract

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

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