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

被引：4
作者：
Wu, Dunqi
Cheng, Xuan
Liu, Yankai
Cheng, Guo
Guan, Xiaoyu
Deng, Qinghai [1 ]
机构：
[1] Shanghai Normal Univ, Key Lab Resource Chem, Educ Minist, Shanghai 200234, Peoples R China
来源：
CHINESE JOURNAL OF ORGANIC CHEMISTRY | 2020年 / 40卷 / 10期
基金：
中国国家自然科学基金;
关键词：
PNN ligand; pincer ligand; asymmetric catalysis; asymmetric allylic alkylation; BETA-KETO-ESTERS; ENANTIOSELECTIVE HYDROGENATION; IRIDIUM CATALYSTS; F-AMPHOX; DIASTEREOSELECTIVE CONSTRUCTION; BIS(OXAZOLINE) LIGANDS; COORDINATION CHEMISTRY; KINETIC RESOLUTION; OXAZOLINE LIGANDS; HIGHLY EFFICIENT;
D O I：
10.6023/cjoc202005090
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A new class of chiral tridentate P,N,N-donor pincer ligands bearing ltwo or three stereocenters, 1-(4,5-dihydrooxazol-2-y1)-N-(2-(diphenylphosphanypbenzyl)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).
引用
收藏
页码：3362 / 3370
页数：9
相关论文
共 75 条
[1]   Non-symmetric pincer ligands: complexes and applications in catalysis [J].
Asay, Matthew ;
Morales-Morales, David .
DALTON TRANSACTIONS, 2015, 44 (40) :17432-17447
[2]   Palladium/N-heterocyclic carbene catalysed regio and diastereoselective reaction of ketones with allyl reagents via inner-sphere mechanism [J].
Bai, Da-Chang ;
Yu, Fei-Le ;
Wang, Wan-Ying ;
Chen, Di ;
Li, Hao ;
Liu, Qing-Rong ;
Ding, Chang-Hua ;
Chen, Bo ;
Hou, Xue-Long .
NATURE COMMUNICATIONS, 2016, 7
[3]   Kinetic Resolution of Unsymmetrical Acyclic Allyl Carbonates Using Trimethylsilyl Cyanide via Palladium-Catalyzed Asymmetric Allylic Alkylation [J].
Bai, Da-Chang ;
Wang, Wan-Ying ;
Ding, Chang-Hua ;
Hou, Xue-Long .
SYNLETT, 2015, 26 (11) :1510-1514
[4]   Expanding the Boxmi Ligand Family: Synthesis and Application of NON and NSN Ligands [J].
Blasius, Clemens K. ;
Ren, Bing-Tao ;
Burgy, David ;
Liu, Yan-Kai ;
Li, Bin ;
Michalsky, Ina ;
Wadepohl, Hubert ;
Deng, Qing-Hai ;
Gade, Lutz H. .
JOURNAL OF ORGANIC CHEMISTRY, 2020, 85 (10) :6719-6731
[5]   Radical Changes in Lewis Acid Catalysis: Matching Metal and Substrate [J].
Bleith, Tim ;
Deng, Qing-Hai ;
Wadepohl, Hubert ;
Gade, Lutz H. .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2016, 55 (27) :7852-7856
[6]   Design and Synthesis of Chiral oxa-Spirocyclic Ligands for Ir-Catalyzed Direct Asymmetric Reduction of Bringmann's Lactones with Molecular H2 [J].
Chen, Gen-Qian ;
Lin, Bi-Jin ;
Huang, Jia-Ming ;
Zhao, Ling-Yu ;
Chen, Qi-Shu ;
Jia, Shi-Peng ;
Yin, Qin ;
Zhang, Xumu .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2018, 140 (26) :8064-8068
[7]   Ir-catalyzed asymmetric hydrogenation of β-keto esters with chiral ferrocenyl P, N, N-ligands [J].
Chen, Xiu-Shuai ;
Hou, Chuan-Jin ;
Qin, Chao ;
Liu, Hongzhu ;
Liu, Yan-Jun ;
Huang, De-Zhi ;
Hu, Xiang-Ping .
RSC ADVANCES, 2017, 7 (21) :12871-12875
[8]   Rational design of sulfoxide-phosphine ligands for Pd-catalyzed enantioselective allylic alkylation reactions [J].
Cheng, Hong-Gang ;
Feng, Bin ;
Chen, Li-Yan ;
Guo, Wei ;
Yu, Xiao-Ye ;
Lu, Liang-Qiu ;
Chen, Jia-Rong ;
Xiao, Wen-Jing .
CHEMICAL COMMUNICATIONS, 2014, 50 (22) :2873-2875
[9]   Iridium-Catalyzed Asymmetric Allylic Substitution Reactions [J].
Cheng, Qiang ;
Tu, Hang-Fei ;
Zheng, Chao ;
Qu, Jian-Ping ;
Helmchen, Guenter ;
You, Shu-Li .
CHEMICAL REVIEWS, 2019, 119 (03) :1855-1969
[10]   Asymmetric Transfer Hydrogenation of Ketones with Well-Defined Manganese(I) PNN and PNNP Complexes [J].
Demmans, Karl Z. ;
Olson, Maxwell E. ;
Morris, Robert H. .
ORGANOMETALLICS, 2018, 37 (24) :4608-4618
12345678