β-Trifluoromethyl α,β-unsaturated Ketones: Efficient Building Blocks for Diverse Trifluoromethylated Molecules

被引:39
作者
Chaudhary, Bharatkumar [1 ]
Kulkarni, Neeraj [1 ]
Saiyed, Nehanaz [1 ]
Chaurasia, Meenakshi [1 ]
Desai, Surbhi [1 ]
Potkule, Sagar [1 ]
Sharma, Satyasheel [2 ]
机构
[1] Ahmedabad NIPER A, Dept Med Chem, Natl Inst Pharmaceut Educ & Res, Gandhinagar 382355, Gujarat, India
[2] Ahmedabad NIPER A, Dept Nat Prod, Natl Inst Pharmaceut Educ & Res, Gandhinagar 382355, Gujarat, India
关键词
Trifluoromethyl group; Fluorinated building blocks; Enones; Conjugate addition; Trifluoromethylated heterocycles; ASYMMETRIC MICHAEL ADDITION; ELECTRON-DEFICIENT ALKENES; ENANTIOSELECTIVE 3+2 CYCLOADDITIONS; FRIEDEL-CRAFTS ALKYLATION; THIOCARBONYL S-METHANIDES; RAUHUT-CURRIER REACTION; CARBON CENTER BEARING; STEREOSELECTIVE-SYNTHESIS; ONE-POT; BETA-TRIFLUOROMETHYL-ALPHA; BETA-UNSATURATED KETONES;
D O I
10.1002/adsc.202001018
中图分类号
O69 [应用化学];
学科分类号
081704 ;
摘要
The trifluoromethyl (CF3) group is an advantageous structural motif in various biologically active molecules as well as materials, which is depicted by steadily increasing demand from the industries involved in drug discovery, agrochemicals and material development. beta-trifluoromethyl alpha,beta-unsaturated carbonyl compounds constitute a very efficient building blocks as starting material in the synthesis of fluorinated molecules. Their usage for the synthesis of various heterocycles and organic molecules bearing stereogenic carbon containing CF3 motif has received significant attention during the recent times. This review provides the existing methods for the synthesis of beta-substituted trifluoromethyl-alpha,beta-unsaturated ketones and the efforts made by researchers for the synthetic development through various reactions by employing them as synthetic building blocks for trifluoromethylated organic scaffolds.
引用
收藏
页码:4794 / 4819
页数:26
相关论文
共 167 条
[61]   New indole alkaloids from Alstonia macrophylla [J].
Kam, TS ;
Choo, YM .
JOURNAL OF NATURAL PRODUCTS, 2004, 67 (04) :547-552
[62]   Catalytic dehydrogenation of aliphatic amines to nitriles, imines, or vinylamines and dealkylation of tertiary aliphatic amines over halide cluster catalysts of group 5 and 6 transition metals [J].
Kamiguchi, S ;
Nakamura, A ;
Suzuki, A ;
Kodomari, M ;
Nomura, M ;
Iwasawa, Y ;
Chihara, T .
JOURNAL OF CATALYSIS, 2005, 230 (01) :204-213
[63]   Quinidine-Catalysed Enantioselective Synthesis of 6-and 4-Trifluoromethyl-Substituted Dihydropyrans [J].
Kasten, Kevin ;
Cordes, David B. ;
Slawin, Alexandra M. Z. ;
Smith, Andrew D. .
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2016, 2016 (21) :3619-3624
[64]  
Kawai H., 2012, ANGEW CHEM, V124, P5043
[65]   Catalytic enantioselective synthesis of β-trifluoromethyl pyrrolines [J].
Kawai, Hiroyuki ;
Kitayama, Takashi ;
Tokunaga, Etsuko ;
Matsumoto, Takashi ;
Sato, Hiroyasu ;
Shiro, Motoo ;
Shibata, Norio .
CHEMICAL COMMUNICATIONS, 2012, 48 (34) :4067-4069
[66]   Partially saturated fluorinated heterocycles: diastereo- and enantioselective synthesis of β-trifluoromethyl-pyrroline carboxylates [J].
Kawai, Hiroyuki ;
Sugita, Yutaka ;
Tokunaga, Etsuko ;
Sato, Hiroyasu ;
Shiro, Motoo ;
Shibata, Norio .
CHEMICAL COMMUNICATIONS, 2012, 48 (30) :3632-3634
[67]   Trifluoromethyl ketones: properties, preparation, and application [J].
Kelly, Christopher B. ;
Mercadante, Michael A. ;
Leadbeater, Nicholas E. .
CHEMICAL COMMUNICATIONS, 2013, 49 (95) :11133-11148
[68]  
Knochel P., 2004, Organic Reactions
[69]   Palladium-catalyzed regio- and stereoselective formate reduction of fluorine-containing allylic mesylates. A new entry for the construction of a tertiary carbon attached with a fluoroalkyl group [J].
Konno, T ;
Takehana, T ;
Mishima, M ;
Ishihara, T .
JOURNAL OF ORGANIC CHEMISTRY, 2006, 71 (09) :3545-3550
[70]   A novel synthesis of trifluoromethylated multi-substituted alkenes via regio- and stereoselective Heck reaction of (E)-4,4,4-trifluoro-1-phenyl-2-buten-1-one [J].
Konno, Tsutomu ;
Yamada, Shigeyuki ;
Tani, Akinori ;
Miyabe, Tomotsugu ;
Ishibara, Takashi .
SYNLETT, 2006, (18) :3025-3028