Nickel-Catalyzed Asymmetric Propargylic Amination of Propargylic Carbonates Bearing an Internal Alkyne Group

被引:46
作者
Watanabe, Kouichi [1 ]
Miyazaki, Yusuke [1 ]
Okubo, Masataka [1 ]
Zhou, Biao [1 ]
Tsuji, Hiroaki [1 ]
Kawatsura, Motoi [1 ]
机构
[1] Nihon Univ, Dept Chem, Coll Humanities & Sci, Setagaya Ku, Tokyo 1568550, Japan
基金
日本学术振兴会;
关键词
SUBSTITUTION-REACTIONS; ENANTIOSELECTIVE PROPARGYLATION; DIRUTHENIUM COMPLEXES; PHENOL DERIVATIVES; AROMATIC-COMPOUNDS; CROSS-COUPLINGS; DYNEMICIN-A; ALCOHOLS; ESTERS; ALKYLATION;
D O I
10.1021/acs.orglett.8b02325
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
We have achieved the nickel-catalyzed asymmetric propargylic amination of propargylic carbonates bearing an internal alkyne group. A wide variety of propargylic carbonates and N-methylaniline derivatives were tolerated under the reaction conditions, providing the corresponding chiral propargylic amines in up to 97% yield with up to 97% ee.
引用
收藏
页码:5448 / 5451
页数:4
相关论文
共 60 条
[1]   Recent Developments in Asymmetric Alkynylation of Imines [J].
Blay, G. ;
Monleon, A. ;
Pedro, J. R. .
CURRENT ORGANIC CHEMISTRY, 2009, 13 (15) :1498-1539
[2]   Addition reactions of mononuclear η3-allenyl/propargyl transition metal complexes:: a new class of potent organometallic carbon electrophiles [J].
Chen, JT .
COORDINATION CHEMISTRY REVIEWS, 1999, 190 :1143-1168
[3]   Ligand Bite Angle-Dependent Palladium-Catalyzed Cyclization of Propargylic Carbonates to 2-Alkynyl Azacycles or Cyclic Dienamides [J].
Daniels, David S. B. ;
Jones, Alison S. ;
Thompson, Amber L. ;
Paton, Robert S. ;
Anderson, Edward A. .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2014, 53 (07) :1915-1920
[4]   Enantioselective copper-catalyzed propargylic amination [J].
Detz, Remko J. ;
Delville, Marielle M. E. ;
Hiemstra, Henk ;
van Maarseveen, Jan H. .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2008, 47 (20) :3777-3780
[5]   Enantioselective Copper-Catalysed Propargylic Substitution: Synthetic Scope Study and Application in Formal Total Syntheses of (+)-Anisomycin and (-)-Cytoxazone [J].
Detz, Remko J. ;
Abiri, Zohar ;
le Griel, Remi ;
Hiemstra, Henk ;
van Maarseveen, Jan H. .
CHEMISTRY-A EUROPEAN JOURNAL, 2011, 17 (21) :5921-5930
[6]   Catalyzed Propargylic Substitution [J].
Detz, Remko J. ;
Hiemstra, Henk ;
van Maarseveen, Jan H. .
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2009, 2009 (36) :6263-6276
[7]   ANTI STEREOSELECTIVITY IN THE PALLADIUM(0)-CATALYZED CONVERSION OF PROPARGYLIC ESTERS INTO ALLENES BY PHENYLZINC CHLORIDE [J].
ELSEVIER, CJ ;
STEHOUWER, PM ;
WESTMIJZE, H ;
VERMEER, P .
JOURNAL OF ORGANIC CHEMISTRY, 1983, 48 (07) :1103-1105
[8]   SYNTHESIS, STRUCTURE, AND REACTIVITY OF SOME (OMICRON-ALLENYL)PALLADIUM(II) AND (OMICRON-PROP-2-YNYL)PALLADIUM(II) COMPLEXES [J].
ELSEVIER, CJ ;
KLEIJN, H ;
BOERSMA, J ;
VERMEER, P .
ORGANOMETALLICS, 1986, 5 (04) :716-720
[9]   Asymmetric Copper-Catalyzed Propargylic Substitution Reaction of Propargylic Acetates with Enamines [J].
Fang, Ping ;
Hou, Xue-Long .
ORGANIC LETTERS, 2009, 11 (20) :4612-4615
[10]   A synthesis of (+)-saxitoxin [J].
Fleming, JJ ;
Du Bois, J .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (12) :3926-3927