NHC catalyzed radical tandem cyclization: an efficient synthesis of α,α-difluoro-γ-lactam derivatives

被引:1
作者
Huang, Tianjiao [1 ]
Yin, Huiping [1 ]
Li, Tuanjie [1 ]
Yu, Chenxia [1 ]
Zhang, Kai [1 ]
Yao, Changsheng [1 ]
机构
[1] Jiangsu Normal Univ, Sch Chem & Mat Sci, Jiangsu Key Lab Green Synthet Chem Funct Mat, Xuzhou 221116, Jiangsu, Peoples R China
基金
中国国家自然科学基金;
关键词
AMINODIFLUOROALKYLATION; LACTAMS; ACID;
D O I
10.1039/d4ob01012d
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Herein, an N-heterocyclic carbene (NHC) catalyzed radical tandem cyclization reaction of N-allylbromodifluoroacetamides and aldehydes has been developed. This method is an efficient protocol for synthesizing alpha,alpha-difluoro-gamma-lactam derivatives in moderate to good yields (27 examples, up to 88% yield and 10 : 1 dr). This strategy features mild and metal-free conditions, high efficiency, and a broad substrate scope. An N-heterocyclic carbene catalyzed radical tandem cyclization reaction of N-allylbromodifluoroacetamides and aldehydes has been developed. This method provides a protocol for synthesizing alpha,alpha-difluoro-gamma-lactam derivatives in moderate to good results (27 examples, up to 88% yield, 10 : 1 d.r.).
引用
收藏
页码:6988 / 6998
页数:11
相关论文
共 53 条
[1]   Synthesis and biological evaluation of novel selective androgen receptor modulators (SARM-s) Part Ill: Discovery of 4-(5-oxopyrrolidine-1-yl) benzonitrile derivative 2f as a clinical candidate [J].
Aikawa, Katsuji ;
Asano, Moriteru ;
Ono, Koji ;
Habuka, Noriyuki ;
Yano, Jason ;
Wilson, Keith ;
Fujita, Hisashi ;
Kandori, Hitoshi ;
Hara, Takahito ;
Morimoto, Megumi ;
Santou, Takashi ;
Yamaoka, Masuo ;
Nakayama, Masaharu ;
Hasuoka, Atsushi .
BIOORGANIC & MEDICINAL CHEMISTRY, 2017, 25 (13) :3330-3349
[2]   Difluoromethylene at the γ-Lactam α-Position Improves 11-Deoxy-8-aza-PGE1 Series EP4 Receptor Binding and Activity: 11-Deoxy-10,10-difluoro-8-aza-PGE1 Analog (KMN-159) as a Potent EP4 Agonist [J].
Barrett, Stephen D. ;
Holt, Melissa C. ;
Kramer, James B. ;
Germain, Bradlee ;
Ho, Chi S. ;
Ciske, Fred L. ;
Kornilov, Andrei ;
Colombo, Joseph M. ;
Uzieblo, Adam ;
O'Malley, James P. ;
Owen, Thomas A. ;
Stein, Adam J. ;
Morano, Maria I. .
JOURNAL OF MEDICINAL CHEMISTRY, 2019, 62 (09) :4731-4741
[3]   Single-electron carbene catalysis in redox processes [J].
Bay, Anna, V ;
Scheidt, Karl A. .
TRENDS IN CHEMISTRY, 2022, 4 (04) :277-290
[4]   Recent advances in the chemistry and applications of N-heterocyclic carbenes [J].
Bellotti, Peter ;
Koy, Maximilian ;
Hopkinson, Matthew N. ;
Glorius, Frank .
NATURE REVIEWS CHEMISTRY, 2021, 5 (10) :711-725
[5]   Organocatalytic umpolung: N-heterocyclic carbenes and beyond [J].
Bugaut, Xavier ;
Glorius, Frank .
CHEMICAL SOCIETY REVIEWS, 2012, 41 (09) :3511-3522
[6]   Radical Reactions with N-Heterocyclic Carbene (NHC)-Derived Acyl Azoliums for Access to Multifunctionalized Ketones [J].
Cai, Hui ;
Yang, Xiaoqun ;
Ren, Shi-Chao ;
Chi, Yonggui Robin .
ACS CATALYSIS, 2024, 14 (11) :8270-8293
[7]   N-heterocyclic carbene-catalyzed radical reactions [J].
Chen, Kun-Quan ;
Sheng, He ;
Liu, Qiang ;
Shao, Pan-Lin ;
Chen, Xiang-Yu .
SCIENCE CHINA-CHEMISTRY, 2021, 64 (01) :7-16
[8]   Fluorination-free synthesis of a 4,4-difluoro-3,3-dimethylproline derivative [J].
Chen, Lijian ;
Kim, Young Mi ;
Kucera, David J. ;
Harrison, Katheryn E. ;
Bahmanyar, Sogole ;
Scott, Jill M. ;
Yazbeck, Daniel .
JOURNAL OF ORGANIC CHEMISTRY, 2006, 71 (15) :5468-5473
[9]   N-HeterocyclicCarbene Organocatalysis: Activation Modes and Typical Reactive Intermediates [J].
Chen, Xingkuan ;
Wang, Hongling ;
Jin, Zhichao ;
Chi, Yonggui Robin .
CHINESE JOURNAL OF CHEMISTRY, 2020, 38 (10) :1167-1202
[10]   Incorporation of a 3-(2,2,2-Trifluoroethyl)-γ-hydroxy-γ-lactam Motif in the Side Chain of 4-Aminoquinolines. Syntheses and Antimalarial Activities [J].
Cornut, Damien ;
Lemoine, Hugues ;
Kanishchev, Oleksandr ;
Okada, Etsuji ;
Albrieux, Florian ;
Beavogui, Abdoul Habib ;
Bienvenu, Anne-Lise ;
Picot, Stephane ;
Bouillon, Jean-Philippe ;
Medebielle, Maurice .
JOURNAL OF MEDICINAL CHEMISTRY, 2013, 56 (01) :73-83