Gold-catalyzed efficient formation of alkenyl enol esters/carbonates from trimethylsilylmethyl-substituted propargyl esters/carbonates

被引:104
作者
Wang, Shaozhong [1 ]
Zhang, Liming [1 ]
机构
[1] Univ Nevada, Dept Chem, Reno, NV 89557 USA
关键词
D O I
10.1021/ol0618151
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
[GRAPHICS] A gold-catalyzed efficient method for the preparation of alkenyl enol esters/carbonates is developed. Besides the mild reaction conditions and high catalytic efficiency, the excellent E-selectivity of the nonenolic double bond is remarkable.
引用
收藏
页码:4585 / 4587
页数:3
相关论文
共 34 条
[1]   Recent applications of gold catalysis in organic synthesis [J].
Arcadi, A ;
Di Giuseppe, S .
CURRENT ORGANIC CHEMISTRY, 2004, 8 (09) :795-812
[2]  
Arcadi A, 2001, ADV SYNTH CATAL, V343, P443, DOI 10.1002/1615-4169(200107)343:5<443::AID-ADSC443>3.3.CO
[3]  
2-R
[4]   The enantioselective Tsuji allylation [J].
Behenna, DC ;
Stoltz, BM .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (46) :15044-15045
[5]   Asymmetric hydrogenation of acyclic enol esters [J].
Boaz, NW .
TETRAHEDRON LETTERS, 1998, 39 (31) :5505-5508
[6]  
Dyker G, 2000, ANGEW CHEM INT EDIT, V39, P4237, DOI 10.1002/1521-3773(20001201)39:23<4237::AID-ANIE4237>3.0.CO
[7]  
2-A
[8]   Non-stabilized transition metal carbenes as intermediates in intramolecular reactions of alkynes with alkenes [J].
Echavarren, AM ;
Nevado, C .
CHEMICAL SOCIETY REVIEWS, 2004, 33 (07) :431-436
[9]   Gold-catalyzed intramolecular reaction of indoles with alkynes: Facile formation of eight-membered rings and an unexpected allenylation [J].
Ferrer, C ;
Echavarren, AM .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2006, 45 (07) :1105-1109
[10]   A STEREOSPECIFIC TOTAL SYNTHESIS OF THE ANTHRACYCLINONES (+/-)-DAUNOMYCINONE AND (+/-)-ISODAUNOMYCINONE [J].
HANSEN, DW ;
PAPPO, R ;
GARLAND, RB .
JOURNAL OF ORGANIC CHEMISTRY, 1988, 53 (18) :4244-4253