Gold(I)-Catalyzed Enantioselective Polycyclization Reactions

被引:164
作者
Sethofer, Steven G. [1 ]
Mayer, Timo [1 ]
Toste, F. Dean [1 ]
机构
[1] Univ Calif Berkeley, Dept Chem, Berkeley, CA 94720 USA
关键词
POLYENE CYCLIZATION; REARRANGEMENTS; CYCLOISOMERIZATIONS; TRITERPENE; GOLD(I);
D O I
10.1021/ja103544p
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
A series of enantioselective polycyclization reactions, catalyzed by a cationic bisphosphine gold complexes, are described. The polycyclization reactions, which employ an alkyne as an initiating group, begin with a gold-promoted 6-exo-dig cyclization and can be terminated with a variety of nucleophiles including carboxylic acids, phenols, sulfonamides, and electron-rich aryl groups. This method allows for the preparation of up to four bonds in a single operation with excellent diastereo- and enantioselectivity.
引用
收藏
页码:8276 / +
页数:3
相关论文
共 49 条
[1]  
Bartlett P.A., 1984, Asymmetric Synthesis, V3B, P341
[2]  
Benitez D, 2009, NAT CHEM, V1, P482, DOI [10.1038/NCHEM.331, 10.1038/nchem.331]
[3]   Enantioselective total synthesis of the kinesin motor protein inhibitor adociasulfate 1 [J].
Bogenstätter, M ;
Limberg, A ;
Overman, LE ;
Tomasi, AL .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1999, 121 (51) :12206-12207
[4]   Gold(I)-catalyzed stereoselective formation of functionalized 2,5-dihydrofurans [J].
Buzas, A ;
Istrate, F ;
Gagosz, F .
ORGANIC LETTERS, 2006, 8 (09) :1957-1959
[5]   Gold(I)-catalyzed formation of 4-alkylidene-1,3-dioxolan-2-ones from propargylic tert-butyl carbonates [J].
Buzas, A ;
Gagosz, F .
ORGANIC LETTERS, 2006, 8 (03) :515-518
[6]   Gold(I)-catalyzed formation of 5-methylene-1,3-oxazolidin-2-ones [J].
Buzas, Andrea ;
Gagosz, Fabien .
SYNLETT, 2006, (17) :2727-2730
[7]   Asymmetric Au(I)-catalyzed synthesis of bicyclo[4.1.0]heptene derivatives via a cycloisomerization process of 1,6-enynes [J].
Chao, Chung-Meng ;
Beltrami, Denis ;
Toullec, Patrick Y. ;
Michelet, Veronique .
CHEMICAL COMMUNICATIONS, 2009, (45) :6988-6990
[8]   Towards asymmetric Au-catalyzed hydroxy- and alkoxycyclization of 1,6-enynes [J].
Chao, Chung-Meng ;
Genin, Emilie ;
Toullec, Patrick Y. ;
Genet, Jean-Pierre ;
Michelet, Veronique .
JOURNAL OF ORGANOMETALLIC CHEMISTRY, 2009, 694 (04) :538-545
[9]   Asymmetric Gold-Catalyzed Hydroarylation/Cyclization Reactions [J].
Chao, Chung-Meng ;
Vitale, Maxime R. ;
Toullec, Patrick Y. ;
Genet, Jean-Pierre ;
Michelet, Veronique .
CHEMISTRY-A EUROPEAN JOURNAL, 2009, 15 (06) :1319-1323
[10]   ZUR KENNTNIS DER TRITERPENE .190. EINE STEREOCHEMISCHE INTERPRETATION DER BIOGENETISCHEN ISOPRENREGEL BEI DEN TRITERPENEN [J].
ESCHENMOSER, A ;
RUZICKA, L ;
JEGER, O ;
ARIGONI, D .
HELVETICA CHIMICA ACTA, 1955, 38 (07) :1890-1904