Gold(I)-Catalyzed Enantioselective Synthesis of Pyrazolidines, Isoxazolidines, and Tetrahydrooxazines

被引:242
作者
LaLonde, R. L. [1 ]
Wang, Z. J. [1 ]
Mba, M. [1 ]
Lackner, A. D. [1 ]
Toste, F. Dean [1 ]
机构
[1] Univ Calif Berkeley, Dept Chem, Berkeley, CA 94720 USA
关键词
asymmetric catalysis; gold; heterocycles; hydroamination; pyrazolidines; OPTICALLY-ACTIVE PYRAZOLIDINE; INTRAMOLECULAR HYDROAMINATION; STEREOSELECTIVE-SYNTHESIS; INTERMOLECULAR HYDROAMINATION; ASYMMETRIC HYDROAMINATION; GOLD CATALYSIS; ALLENES; CYCLOISOMERIZATION; HYDROARYLATION; CYCLOADDITION;
D O I
10.1002/anie.200905000
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
(Figure Presented) (Figure Presented) Au-ff on a trip: Chiral ligands (L) and chiral anions [(S)-TriPAg] are employed in the gold(I)-catalyzed enantioselective intramolecular additions of hydrazines and hydroxylamines to allenes. These complementary methods allow access to chiral vinyl isoxazolidines, oxazines, and differentially protected pyrazolidines. PNB = para-nitrobenzoyl. © 2010 Wiley-VCH Verlag GmbH & Co. KGaA.
引用
收藏
页码:598 / 601
页数:4
相关论文
共 42 条
[1]   Synthesis of sedamine by cycloisomerisation of an allenic hydroxylamine [J].
Bates, Roderick W. ;
Nemeth, Joseph A. ;
Snell, Robert H. .
SYNTHESIS-STUTTGART, 2008, (07) :1033-1038
[2]   Stereochemical promiscuity in artificial transcriptional activators [J].
Buhrlage, SJ ;
Brennan, BB ;
Minter, AR ;
Mapp, AK .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (36) :12456-12457
[3]   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
[4]  
Garcia-Garcia P., 2009, Angew. Chem, V121, P4427, DOI DOI 10.1038/NMETH.3579
[5]   A Powerful Chiral Counteranion Motif for Asymmetric Catalysis [J].
Garcia-Garcia, Pilar ;
Lay, Frank ;
Garcia-Garcia, Patricia ;
Rabalakos, Constantinos ;
List, Benjamin .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2009, 48 (24) :4363-4366
[6]   Stereoselective synthesis of cis- or trans-3,5-disubstituted pyrazolidines via Pd-catalyzed carboamination reactions:: Use of allylic strain to control product stereochemistry through N-substituent manipulation [J].
Giampietro, Natalie C. ;
Wolfe, John P. .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2008, 130 (39) :12907-12911
[7]  
Hamilton GL, 2007, SCIENCE, V317, P496, DOI 10.1126/science.1145229
[8]   Pyridinium 1,1′-Binaphthyl-2,2′-disulfonates as Highly Effective Chiral Bronsted Acid-Base Combined Salt Catalysts for Enantioselective Mannich-Type Reaction [J].
Hatano, Manabu ;
Maki, Toshikatsu ;
Moriyama, Katsuhiko ;
Arinobe, Manabu ;
Ishihara, Kazuaki .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2008, 130 (50) :16858-+
[9]   Catalytic intramolecular hydroamination of substituted aminoallenes by chiral titanium amino-alcohol complexes [J].
Hoover, JM ;
Petersen, JR ;
Pikul, JH ;
Johnson, AR .
ORGANOMETALLICS, 2004, 23 (20) :4614-4620
[10]   Catalytic asymmetric hydroamination of non-activated olefins [J].
Hultzsch, KC .
ORGANIC & BIOMOLECULAR CHEMISTRY, 2005, 3 (10) :1819-1824