Microwave-promoted three-component coupling of aldehyde, alkyne, and amine via C-H activation catalyzed by copper in water

被引：304
作者：
Shi, L
Tu, YQ [1 ]
Wang, M
Zhang, FM
Fan, CA
机构：
[1] Lanzhou Univ, Dept Chem, Lanzhou 730000, Peoples R China
[2] Lanzhou Univ, State Key Lab Appl Organ Chem, Lanzhou 730000, Peoples R China
来源：
ORGANIC LETTERS | 2004年 / 6卷 / 06期
关键词：
D O I：
10.1021/ol049936t
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
[GRAPHICS] An efficient three-component coupling of aldehyde, alkyne, and amine to generate propargylamines has been effected under microwave irradiation in water using only Cul catalyst without the noble metal cocatalyst. This method has proved to be applicable to a wide range of substrates. In addition, the preliminary experiment using (S)-proline methyl ester as a chiral source demonstrated that it could be developed to be a direct and highly diastereoselective method for construction of chiral propargylamines.
引用
收藏
页码：1001 / 1003
页数：3
相关论文
共 37 条
[1]   Three-component enantioselective synthesis of propargylamines through Zr-catalyzed additions of alkyl zinc reagents to alkynylimines [J].
Akullian, LC ;
Snapper, ML ;
Hoveyda, AH .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2003, 42 (35) :4244-4247
[2]   BF3-mediated addition of lithium phenylacetylide to an imine:: Correlations of structures and reactivities.: BF3•R3N derivatives as substitutes for BF3•Et2O [J].
Aubrecht, KB ;
Winemiller, MD ;
Collum, DB .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2000, 122 (45) :11084-11089
[3]   ADDITION OF ORGANOMETALLIC REAGENTS TO N-GLYCOSYL NITRONES - ENANTIOSELECTIVE SYNTHESES OF (+)-(R)-ZILEUTON AND (-)-(S)-ZILEUTON [J].
BASHA, A ;
HENRY, R ;
MCLAUGHLIN, MA ;
RATAJCZYK, JD ;
WITTENBERGER, SJ .
JOURNAL OF ORGANIC CHEMISTRY, 1994, 59 (20) :6103-6106
[4]   Additions of organometallic reagents to C=N bonds: Reactivity and selectivity [J].
Bloch, R .
CHEMICAL REVIEWS, 1998, 98 (04) :1407-1438
[5]  
Boulton AA, 1997, DRUG DEVELOP RES, V42, P150, DOI 10.1002/(SICI)1098-2299(199711/12)42:3/4<150::AID-DDR6>3.0.CO
[6]  
2-P
[7]   Diastereoselective synthesis of heterosubstituted organogembismetallic reagents. Application to a new propargylmetalation reaction of vinyl metals. [J].
Brasseur, D ;
Marek, I ;
Normant, JF .
TETRAHEDRON, 1996, 52 (21) :7235-7250
[8]   Organometallic-type reactions in aqueous media mediated by indium: Application to the synthesis of carbohydrates [J].
Chan, TH ;
Isaac, MB .
PURE AND APPLIED CHEMISTRY, 1996, 68 (04) :919-924
[9]   ENANTIOSELECTIVE SYNTHESIS OF PRIMARY AMINES VIA GRIGNARD ADDITIONS TO STEREOGENIC N-(ALPHA-PHENYL-BETA-(BENZYLOXY)ETHYL)NITRONES [J].
CHANG, ZY ;
COATES, RM .
JOURNAL OF ORGANIC CHEMISTRY, 1990, 55 (11) :3475-3483
[10]   DIASTEREOSELECTIVITY OF ORGANOMETALLIC ADDITIONS TO NITRONES BEARING STEREOGENIC N-SUBSTITUENTS [J].
CHANG, ZY ;
COATES, RM .
JOURNAL OF ORGANIC CHEMISTRY, 1990, 55 (11) :3464-3474
1234