Development of the Pictet-Spengler reaction catalyzed by AuCl3/AgOTf

被引:107
作者
Youn, SW [1 ]
机构
[1] Pukyong Natl Univ, Dept Chem, Pusan 608737, South Korea
关键词
D O I
10.1021/jo0524775
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
[GRAPHICS] Mild and efficient AUCl(3)/AgOTf-catalyzed Pictet-Spengler reactions were developed to afford in good yields a variety of tetrahydroisoquinoline and tetrahydro-beta-carboline ring systems, which constitute important motifs in biologically active natural and synthetic organic compounds.
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页码:2521 / 2523
页数:3
相关论文
共 18 条
[1]   β-phenylethylamines and the isoquinoline alkaloids [J].
Bentley, KW .
NATURAL PRODUCT REPORTS, 2004, 21 (03) :395-424
[2]  
Brown R. T, 1983, INDOLES 4
[3]   THE PICTET-SPENGLER CONDENSATION - A NEW DIRECTION FOR AN OLD REACTION [J].
COX, ED ;
COOK, JM .
CHEMICAL REVIEWS, 1995, 95 (06) :1797-1842
[4]   Pictet-Spengler reactions in multiphasic supercritical carbon dioxide/CO2-expanded liquid media.: In situ generation of carbamates as a strategy for reactions of amines in supercritical carbon dioxide [J].
Dunetz, JR ;
Ciccolini, RP ;
Fröling, M ;
Paap, SM ;
Allen, AJ ;
Holmes, AB ;
Tester, JW ;
Danheiser, RL .
CHEMICAL COMMUNICATIONS, 2005, (35) :4465-4467
[5]  
Hashmi ASK, 2004, GOLD BULL, V37, P51
[6]   Homogeneous gold catalysts and alkynes: A successful liaison [J].
Hashmi, ASK .
GOLD BULLETIN, 2003, 36 (01) :3-9
[7]   Microwave accelerated Pictet-Spengler reactions of tryptophan with ketones directed toward the preparation of 1,1-disubstituted indole alkaloids [J].
Kuo, FM ;
Tseng, MC ;
Yen, YH ;
Chu, YH .
TETRAHEDRON, 2004, 60 (52) :12075-12084
[8]   A highly efficient gold/silver-catalyzed addition of arenes to imines [J].
Luo, YM ;
Li, CJ .
CHEMICAL COMMUNICATIONS, 2004, (17) :1930-1931
[9]   Cyclizations of N-acyliminium ions [J].
Maryanoff, BE ;
Zhang, HC ;
Cohen, JH ;
Turchi, IJ ;
Maryanoff, CA .
CHEMICAL REVIEWS, 2004, 104 (03) :1431-1628
[10]   Stereoselectivity of superacid-catalyzed Pictet-Spengler cyclization reactions [J].
Nakamura, S ;
Tanaka, M ;
Taniguchi, T ;
Uchiyama, M ;
Ohwada, T .
ORGANIC LETTERS, 2003, 5 (12) :2087-2090