Photoinduced Kochi Decarboxylative Elimination for the Synthesis of Enamides and Enecarbamates from N-Acyl Amino Acids

被引:42
作者
Cartwright, Kaitie C. [1 ]
Lang, Simon B. [1 ]
Tunge, Jon A. [1 ]
机构
[1] Univ Kansas, Dept Chem, 2010 Malott Hall,1251 Wescoe Hall Dr, Lawrence, KS 66045 USA
基金
美国国家科学基金会;
关键词
ELECTRON-TRANSFER OXIDATION; ALKYL RADICALS; ISOMERIZATION; HYDROAMINATION; ALKENES; REDUCTION; AMIDES; ALLYLAMIDES; RUTHENIUM; AMINATION;
D O I
10.1021/acs.joc.9b00167
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Decarboxylative elimination of easily accessible N-acyl amino acids to provide enamide and enecarbamate building blocks has been realized through the combination of an organophotoredox catalyst and copper acetate as the terminal oxidant. This operationally simple process utilizes inexpensive and readily available reagents without preactivation of the carboxylic acid. Enamides and enecarbamates are now accessible directly from N-acyl amino acids consequently improving upon the utility of Kochi's oxidative decarboxylation of carboxylic acids.
引用
收藏
页码:2933 / 2940
页数:8
相关论文
共 51 条
[21]  
Kuramochi K, 2000, SYNLETT, P397
[22]   Stereoselective Alkene Isomerization over One Position [J].
Larsen, Casey R. ;
Grotjahn, Douglas B. .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2012, 134 (25) :10357-10360
[23]   CHEMISTRY OF IMINES [J].
LAYER, RW .
CHEMICAL REVIEWS, 1963, 63 (05) :489-+
[24]   Enantioselective Friedel-Crafts reactions between phenols and N-tosylaldimines catalyzed by a leucine-derived bifunctional catalyst [J].
Li, Guo-Xing ;
Qu, Jin .
CHEMICAL COMMUNICATIONS, 2012, 48 (44) :5518-5520
[25]   Allenamides: A Powerful and Versatile Building Block in Organic Synthesis [J].
Lu, Ting ;
Lu, Zhenjie ;
Ma, Zhi-Xiong ;
Zhang, Yu ;
Hsung, Richard P. .
CHEMICAL REVIEWS, 2013, 113 (07) :4862-4904
[26]   Enamides and enecarbamates as nucleophiles in stereoselective C-C and C-N bond-forming reactions [J].
Matsubara, Ryosuke ;
Kobayashi, Shu .
ACCOUNTS OF CHEMICAL RESEARCH, 2008, 41 (02) :292-301
[27]   Photocatalytic E Z Isomerization of Alkenes [J].
Metternich, J. B. ;
Gilmour, R. .
SYNLETT, 2016, 27 (18) :2541-2552
[28]   Enamides Accessed from Aminothioesters via a Pd(0)-Catalyzed Decarbonylative/β-Hydride Elimination Sequence [J].
Min, Geanna K. ;
Hernandez, Dacil ;
Lindhardt, Anders T. ;
Skrydstrup, Troels .
ORGANIC LETTERS, 2010, 12 (21) :4716-4719
[29]   Hydroamination:: Direct addition of amines to alkenes and alkynes [J].
Mueller, Thomas E. ;
Hultzsch, Kai C. ;
Yus, Miguel ;
Foubelo, Francisco ;
Tada, Mizuki .
CHEMICAL REVIEWS, 2008, 108 (09) :3795-3892
[30]   THE WITTIG OLEFINATION REACTION WITH CARBONYL-COMPOUNDS OTHER THAN ALDEHYDES AND KETONES [J].
MURPHY, PJ ;
BRENNAN, J .
CHEMICAL SOCIETY REVIEWS, 1988, 17 (01) :1-30