Highly Selective Construction of Medium-Sized Lactams by Palladium-Catalyzed Intramolecular Hydroaminocarbonylation of Aminoalkynes

被引：34
作者：
Hu, Yue [1 ,3 ]
Huang, Hanmin [1 ,2 ]
机构：
[1] Chinese Acad Sci, Lanzhou Inst Chem Phys, State Key Lab Oxo Synth & Select Oxidat, Lanzhou 730000, Gansu, Peoples R China
[2] Univ Sci & Technol China, Dept Chem, Hefei 230026, Anhui, Peoples R China
[3] Univ Chinese Acad Sci, Beijing 100049, Peoples R China
来源：
ORGANIC LETTERS | 2017年 / 19卷 / 19期
基金：
中国国家自然科学基金;
关键词：
RING-CLOSING METATHESIS; CARBONYLATION REACTIONS; EFFICIENT SYNTHESIS; BETA-LACTAMS; AMINOCARBONYLATION; ALKENES; HETEROCYCLES; NITROGEN; ALKYNES; ANTIBIOTICS;
D O I：
10.1021/acs.orglett.7b02284
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A novel palladium-catalyzed intramolecular hydro-aminocarbonylation of aminoalkynes has been developed. This direct and operationally simple protocol provides a rapid and reliable approach to a diverse array of valuable seven- and eight-membered lactams with high chemoselectivity and regioselectivity. The high selectivity might be attributed to rational tuning the electronic nature of the amine moiety and the palladium catalyst, which enabled this transformation to proceed in the absence of acidic or any other additives under fairly mild reaction conditions. This method paves the way for the synthesis of medium-sized lactams.
引用
收藏
页码：5070 / 5073
页数：4
相关论文
共 47 条
[1]   Synthesis and structure activity relationships of novel non-peptidic metallo-aminopeptidase inhibitors [J].
Albrecht, Sebastien ;
Defoin, Albert ;
Salomon, Emmanuel ;
Tarnus, Celine ;
Wetterholm, Anders ;
Haeggstrom, Jasper Z. .
BIOORGANIC & MEDICINAL CHEMISTRY, 2006, 14 (21) :7241-7257
[2]   Magnesium Chelating 2-Hydroxyisoquinoline-1,3(2H,4H)-diones, as Inhibitors of HIV-1 Integrase and/or the HIV-1 Reverse Transcriptase Ribonuclease H Domain: Discovery of a Novel Selective Inhibitor of the Ribonuclease H Function [J].
Billamboz, Muriel ;
Bailly, Fabrice ;
Lion, Cedric ;
Touati, Nadia ;
Vezin, Herve ;
Calmels, Christina ;
Andreola, Marie-Line ;
Christ, Frauke ;
Debyser, Zeger ;
Cotelle, Philippe .
JOURNAL OF MEDICINAL CHEMISTRY, 2011, 54 (06) :1812-1824
[3]   Palladium-Catalyzed Intermolecular Aminocarbonylation of Alkenes: Efficient Access of β-Amino Acid Derivatives [J].
Cheng, Jiashun ;
Qi, Xiaoxu ;
Li, Ming ;
Chen, Pinhong ;
Liu, Guosheng .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2015, 137 (07) :2480-2483
[4]   Palladium-Catalyzed Carbocyclization of Alkynyl Ketones Proceeding through a Carbopalladation Pathway [J].
Chernyak, Natalia ;
Gorelsky, Serge I. ;
Gevorgyan, Vladimir .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2011, 50 (10) :2342-2345
[5]   Design, synthesis, and conformational analysis of eight-membered cyclic peptidomimetics prepared using ring closing metathesis [J].
Creighton, CJ ;
Du, YM ;
Reitz, AB .
BIOORGANIC & MEDICINAL CHEMISTRY, 2004, 12 (16) :4375-4385
[6]   Intramolecular Staudinger ligation:: A powerful ring-closure method to form medium-sized lactams [J].
David, O ;
Meester, WJN ;
Bieräugel, H ;
Schoemaker, HE ;
Hiemstra, H ;
van Maarseveen, JH .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2003, 42 (36) :4373-4375
[7]   MEDIUM RING NITROGEN-HETEROCYCLES [J].
EVANS, PA ;
HOLMES, AB .
TETRAHEDRON, 1991, 47 (44) :9131-9166
[8]   Selective Palladium-Catalyzed Aminocarbonylation of 1,3-Dienes: Atom-Efficient Synthesis of β,γ-Unsaturated Amides [J].
Fang, Xianjie ;
Li, Haoquan ;
Jackstell, Ralf ;
Beller, Matthias .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2014, 136 (45) :16039-16043
[9]   Selective Palladium-Catalyzed Aminocarbonylation of Olefins with Aromatic Amines and Nitroarenes [J].
Fang, Xianjie ;
Jackstell, Ralf ;
Beller, Matthias .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2013, 52 (52) :14089-14093
[10]  
Faulkner DJ, 1999, NAT PROD REP, V16, P155
12345