Cycle-Specific Organocascade Catalysis: Application to Olefin Hydroamination, Hydro-oxidation, and Amino-oxidation, and to Natural Product Synthesis

被引:209
作者
Simmons, Bryon [1 ]
Walji, Abbas M. [1 ]
MacMillan, David W. C. [1 ]
机构
[1] Princeton Univ, Merck Ctr Catalysis, Princeton, NJ 08544 USA
关键词
cascade reactions; enantioselectivity; natural products; organocatalysis; ASYMMETRIC ALPHA-AMINATION; ENAMINE CATALYSIS; DIAMINATION; STRATEGY; DESIGN; ROUTE;
D O I
10.1002/anie.200900220
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
United in effort: The combined application of iminium (Im) and enamine (En) catalysts can effect a range of valuable asymmetric transformations including 1,2-hydroamination, - hydro-oxidation, and -amino-oxidation of olefins (see picture). An enantioselective organocascade catalysis was also applied in the synthesis of a complex natural product. © 2009 Wiley-VCH Verlag GmbH & Co. KGaA.
引用
收藏
页码:4349 / 4353
页数:5
相关论文
共 46 条
[31]   Antifungal aromadendrane sesquiterpenoids from the leaves of Xylopia brasiliensis [J].
Moreira, IC ;
Lago, JHG ;
Young, MCM ;
Roque, NF .
JOURNAL OF THE BRAZILIAN CHEMICAL SOCIETY, 2003, 14 (05) :828-831
[32]   Hydroamination:: Direct addition of amines to alkenes and alkynes [J].
Mueller, Thomas E. ;
Hultzsch, Kai C. ;
Yus, Miguel ;
Foubelo, Francisco ;
Tada, Mizuki .
CHEMICAL REVIEWS, 2008, 108 (09) :3795-3892
[33]   A first asymmetric diamination of olefins [J].
Muñiz, K ;
Nieger, M .
SYNLETT, 2003, (02) :211-214
[34]  
Nilov D, 2002, ADV SYNTH CATAL, V344, P1169, DOI 10.1002/1615-4169(200212)344:10<1169::AID-ADSC1169>3.0.CO
[35]  
2-G
[36]  
Rigby J.H., 1988, SYNTHESIS-STUTTGART, P188
[37]   A highly enantioselective bronsted acid catalyzed cascade reaction: Organocatalytic transfer hydrogenation of quinolines and their application in the synthesis of alkaloids [J].
Rueping, Magnus ;
Antonchick, Andrey R. ;
Theissmann, Thomas .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2006, 45 (22) :3683-3686
[38]   Organocatalytic asymmetric Mannich reactions: New methodology, catalyst design, and synthetic applications [J].
Ting, Amal ;
Schaus, Scott E. .
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2007, 2007 (35) :5797-5815
[39]   Strategies to bypass the taxol problem. Enantioselective cascade catalysis, a new approach for the efficient construction of molecular complexity [J].
Walji, Abbas M. ;
MacMillan, David W. C. .
SYNLETT, 2007, (10) :1477-1489
[40]   Toward the ideal synthesis. New transition metal-catalyzed reactions inspired by novel medicinal leads [J].
Wender, PA ;
Bi, FC ;
Gamber, GG ;
Gosselin, F ;
Hubbard, RD ;
Scanio, MJC ;
Sun, R ;
Williams, TJ ;
Zhang, L .
PURE AND APPLIED CHEMISTRY, 2002, 74 (01) :25-31