Ni-Catalyzed enantioselective reductive aryl-alkenylation of alkenes: application to the synthesis of (+)-physovenine and (+)-physostigmine

被引:64
作者
Li, Yuxiu [1 ]
Ding, Zhengtian [1 ]
Lei, Aiwen [1 ]
Kong, Wangqing [1 ]
机构
[1] Wuhan Univ, Coll Chem & Mol Sci, IAS, Wuhan 430072, Hubei, Peoples R China
基金
中国国家自然科学基金;
关键词
CROSS-COUPLING REACTIONS; ANION CAPTURE PROCESSES; FORMAL TOTAL SYNTHESIS; ASYMMETRIC-SYNTHESIS; CALABAR ALKALOIDS; CYCLIZATION; OXINDOLES; HALIDES; ROUTE; DICARBOFUNCTIONALIZATION;
D O I
10.1039/c9qo00744j
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A Ni-catalyzed enantioselective reductive aryl-alkenylation of alkenes by cyclizative coupling of an aryl bromide and a vinyl bromide is developed, providing efficient access to functionalized 3,3-disubstituted oxindoles under mild conditions, without requiring the use of preformed vinylmetallic reagents. With this method, a concise formal synthesis of (+)-physovenine and (+)-physostigmine has been completed.
引用
收藏
页码:3305 / 3309
页数:5
相关论文
共 52 条
[1]   BIOACTIVE ALKALOIDS .4. RESULTS OF RECENT INVESTIGATIONS WITH COLCHICINE AND PHYSOSTIGMINE [J].
BROSSI, A .
JOURNAL OF MEDICINAL CHEMISTRY, 1990, 33 (09) :2311-2319
[2]  
Cherney A. H., 2015, J AM CHEM SOC, V137, P10480
[3]   Enantioselective and Enantiospecific Transition-Metal-Catalyzed Cross-Coupling Reactions of Organometallic Reagents To Construct C-C Bonds [J].
Cherney, Alan H. ;
Kadunce, Nathaniel T. ;
Reisman, Sarah E. .
CHEMICAL REVIEWS, 2015, 115 (17) :9587-9652
[4]   Nickel-Catalyzed Asymmetric Reductive Cross-Coupling Between Vinyl and Benzyl Electrophiles [J].
Cherney, Alan H. ;
Reisman, Sarah E. .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2014, 136 (41) :14365-14368
[5]   Catalytic Asymmetric Reductive Acyl Cross-Coupling: Synthesis of Enantioenriched Acyclic α,α-Disubstituted Ketones [J].
Cherney, Alan H. ;
Kadunce, Nathaniel T. ;
Reisman, Sarah E. .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2013, 135 (20) :7442-7445
[6]   Recent advances in organocatalytic methods for the synthesis of disubstituted 2-and 3-indolinones [J].
Dalpozzo, Renato ;
Bartoli, Giuseppe ;
Bencivenni, Giorgio .
CHEMICAL SOCIETY REVIEWS, 2012, 41 (21) :7247-7290
[7]  
David R., 2019, ANGEW CHEM INT EDIT, V58, P3198
[8]   The Akuammiline Alkaloids; Origin and Synthesis [J].
Eckermann, Ruben ;
Gaich, Tanja .
SYNTHESIS-STUTTGART, 2013, 45 (20) :2813-2823
[9]   An expedient route to the calabar bean alkaloids (-)-physovenine and (-)-physostigmine [J].
El-Azab, AS ;
Taniguchi, T ;
Ogasawara, K .
ORGANIC LETTERS, 2000, 2 (18) :2757-2759
[10]   Cross-Electrophile Coupling: Principles of Reactivity and Selectivity [J].
Everson, Daniel A. ;
Weix, Daniel J. .
JOURNAL OF ORGANIC CHEMISTRY, 2014, 79 (11) :4793-4798