Bio- and Medicinally Compatible α-Amino-Acid Modification via Merging Photoredox and N-Heterocyclic Carbene Catalysis

被引:28
作者
Du, Ding [1 ]
Zhang, Kuili [1 ]
Ma, Rui [1 ]
Chen, Lei [1 ]
Gao, Jian [1 ]
Lu, Tao [1 ]
Shi, Zhihao [1 ]
Feng, Jie [1 ]
机构
[1] China Pharmaceut Univ, Dept Organ Chem, State Key Lab Nat Med, Nanjing 210009, Peoples R China
基金
中国国家自然科学基金;
关键词
AZA-BENZOIN REACTIONS; KETONES; ALKYLATION; OXIDATION; ALDEHYDES; ENALS;
D O I
10.1021/acs.orglett.0c02202
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
An N-heterocyclic carbene and photoredox cocatalyzed alpha-amino-acid decarboxylative carbonylation reaction is presented. This method displays good scope generality, providing a direct pathway to access various downstream alpha-amino ketones under bio- and medicinally compatible conditions. Moreover, this strategy is appealing to chemical biology because it has great potential for the chemical modification of peptides or the late-stage synthesis of keto-peptides.
引用
收藏
页码:6370 / 6375
页数:6
相关论文
共 58 条
[41]   Decarboxylative Csp3- N Bond Formation by Electrochemical Oxidation of Amino Acids [J].
Shao, Xiaoqing ;
Zheng, Yue ;
Tian, Lifang ;
Martin-Torres, Inmaculada ;
Echavarren, Antonio M. ;
Wang, Yahui .
ORGANIC LETTERS, 2019, 21 (22) :9262-9267
[42]   Organophotoredox-Catalyzed Decarboxylative C(sp3)-O Bond Formation [J].
Shibutani, Shotaro ;
Kodo, Taiga ;
Takeda, Mitsutaka ;
Nagao, Kazunori ;
Tokunaga, Norihito ;
Sasaki, Yusuke ;
Ohmiya, Hirohisa .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2020, 142 (03) :1211-1216
[43]   Transition Metal Catalyzed Enantioselective α-Heterofunctionalization of Carbonyl Compounds [J].
Smith, Alexander M. R. ;
Hii, King Kuok .
CHEMICAL REVIEWS, 2011, 111 (03) :1637-1656
[44]   Enantioselective N-Heterocyclic Carbene Catalyzed Aza-Benzoin Reaction of Enals with Activated Ketimines [J].
Sun, Li-Hui ;
Liang, Zhi-Qin ;
Jia, Wen-Qiang ;
Ye, Song .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2013, 52 (22) :5803-5806
[45]   Synthesis of Carfentanil Amide Opioids Using the Ugi Multicomponent Reaction [J].
Varadi, Andras ;
Palmer, Travis C. ;
Haselton, Nathan ;
Afonin, Daniel ;
Subrath, Joan J. ;
Le Rouzic, Valerie ;
Hunkele, Amanda ;
Pasternak, Gavril W. ;
Marrone, Gina F. ;
Borics, Attila ;
Majumdar, Susruta .
ACS CHEMICAL NEUROSCIENCE, 2015, 6 (09) :1570-1577
[46]   Cooperative Catalysis and Activation with N-Heterocyclic Carbenes [J].
Wang, Michael H. ;
Scheidt, Karl A. .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2016, 55 (48) :14912-14922
[47]   Nucleophilic (Radio)Fluorination of Redox-Active Esters via Radical-Polar Crossover Enabled by Photoredox Catalysis [J].
Webb, Eric W. ;
Park, John B. ;
Cole, Erin L. ;
Donnelly, David J. ;
Bonacorsi, Samuel J. ;
Ewing, William R. ;
Doyle, Abigail G. .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2020, 142 (20) :9493-9500
[48]   Asymmetric Synthesis of α-Amino Ketones by Bronsted Acid Catalysis [J].
Wen, Wei ;
Zeng, Yu ;
Peng, Li-Yu ;
Fu, Li-Na ;
Guo, Qi-Xiang .
ORGANIC LETTERS, 2015, 17 (15) :3922-3925
[49]   N-Heterocyclic carbene/photo-cocatalyzed oxidative Smiles rearrangement: synthesis of aryl salicylates from O-aryl salicylaldehydes [J].
Xia, Zi-Hao ;
Dai, Lei ;
Gao, Zhong-Hua ;
Ye, Song .
CHEMICAL COMMUNICATIONS, 2020, 56 (10) :1525-1528
[50]   N-Heterocyclic Carbene-Catalyzed Chemoselective Cross-Aza-Benzoin Reaction of Enals with Isatin-Derived Ketimines: Access to Chiral Quaternary Aminooxindoles [J].
Xu, Jianfeng ;
Mou, Chengli ;
Zhu, Tingshun ;
Song, Bao-An ;
Chi, Yonggui Robin .
ORGANIC LETTERS, 2014, 16 (12) :3272-3275