Asymmetric bis(oxazoline)-Ni(ii) catalyzed α-hydroxylation of cyclic β-keto esters under visible light

被引:8
作者
Yin, Hao [1 ]
Wang, Chao-Jie [1 ]
Zhao, Yu-Gen [1 ]
He, Zi-Yang [1 ]
Chu, Ming-Ming [2 ]
Wang, Yi-Feng [1 ]
Xu, Dan-Qian [1 ]
机构
[1] Zhejiang Univ Technol, Dept Green Chem & Technol, State Key Lab Breeding Base Green Chem Synth Tech, Key Lab Green Pesticides & Cleaner Prod Technol Z, Hangzhou 310014, Peoples R China
[2] Jiaxing Univ, Coll Biol Chem Sci & Engn, Jiaxing 314001, Peoples R China
关键词
PHASE-TRANSFER CATALYSTS; COMPLEXES; FLUORINATION; RESOLUTION; OXIDATION; LIGANDS;
D O I
10.1039/d1ob00546d
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Using visible light as a driving force and molecular oxygen as a green oxidant, we developed bis(oxazoline)-Ni(acac)(2) catalyzed asymmetric alpha-hydroxylation of beta-keto esters under low photosensitizer loading, and the protocol enabled an efficient transformation to provide the desired chiral alpha-hydroxy-beta-keto esters in high yields (up to 99%) and enantioselectivities (up to 99% ee) at room temperature.
引用
收藏
页码:6588 / 6592
页数:6
相关论文
共 41 条
[1]   Organocatalytic asymmetric hydroxylation of β-keto esters:: Metal-free synthesis of optically active anti-diols [J].
Acocella, MR ;
Mancheño, OG ;
Bella, M ;
Jorgensen, KA .
JOURNAL OF ORGANIC CHEMISTRY, 2004, 69 (23) :8165-8167
[2]   Applications of Pybox Complexes in Asymmetric Catalysis [J].
Babu, Sheba Ann ;
Krishnan, K. Keerthi ;
Ujwaldev, S. M. ;
Anilkumar, Gopinathan .
ASIAN JOURNAL OF ORGANIC CHEMISTRY, 2018, 7 (06) :1033-1053
[3]   Zirconium-Salan Catalyzed Enantioselective α-Hydroxylation of β-Keto Esters [J].
Chen, Jie ;
Gu, Haiyang ;
Zhu, Xueying ;
Nam, Wonwoo ;
Wang, Bin .
ADVANCED SYNTHESIS & CATALYSIS, 2020, 362 (14) :2976-2983
[4]   Straightforward synthesis of (R)-(-)-Kjellmanianone [J].
Christoffers, J ;
Werner, T ;
Frey, W ;
Baro, A .
CHEMISTRY-A EUROPEAN JOURNAL, 2004, 10 (04) :1042-1045
[5]   C2-symmetric chiral bis(oxazoline) ligands in asymmetric catalysis [J].
Desimoni, Giovanni ;
Faita, Giuseppe ;
Jorgensen, Karl Anker .
CHEMICAL REVIEWS, 2006, 106 (09) :3561-3651
[6]   Bifunctional Photocatalysts for Enantioselective Aerobic Oxidation of β-Ketoesters [J].
Ding, Wei ;
Lu, Liang-Qiu ;
Quan-Quan Zhou ;
Wei, Yi ;
Chen, Jia-Rong ;
Xiao, Wen-Jing .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2017, 139 (01) :63-66
[7]   Asymmetry on large scale: The roadmap to stereoselective processes [J].
Federsel, HJ .
NATURE REVIEWS DRUG DISCOVERY, 2005, 4 (08) :685-697
[8]   Iron(III)-salan complexes catalysed highly enantioselective fluorination and hydroxylation of β-keto esters and N-Boc oxindoles [J].
Gu, Xin ;
Zhang, Yan ;
Xu, Zhen-Jiang ;
Che, Chi-Ming .
CHEMICAL COMMUNICATIONS, 2014, 50 (58) :7870-7873
[9]   Lewis acid-catalyzed enantioselective hydroxylation reactions of oxindoles and β-keto esters using DBFOX ligand [J].
Ishimaru, Takehisa ;
Shibata, Norio ;
Nagai, Jun ;
Nakamura, Shuichi ;
Toru, Takeshi ;
Kanemasa, Shuji .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (51) :16488-16489
[10]   Dibenzofuran-4,6-bis(oxazoline) (DBFOX). A novel trans-chelating bis(oxazoline) ligand for asymmetric reactions [J].
Itoh, Kennosuke ;
Sibi, Mukund P. .
ORGANIC & BIOMOLECULAR CHEMISTRY, 2018, 16 (31) :5551-5565