Enantioselective Nazarov reactions through catalytic asymmetric proton transfer

被引:180
作者
Liang, GX [1 ]
Trauner, D [1 ]
机构
[1] Univ Calif Berkeley, Dept Chem, Ctr New Direct Organ Synth, Berkeley, CA 94720 USA
关键词
D O I
10.1021/ja0476664
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
The development of catalytic asymmetric Nazarov reactions that require only 10 mol % of chiral Lewis acid and proceed with ee's between 72% and 97% is described. Copyright © 2004 American Chemical Society.
引用
收藏
页码:9544 / 9545
页数:2
相关论文
共 28 条
[1]   Catalytic asymmetric nazarov reactions promoted by chiral Lewis acid complexes [J].
Aggarwal, VK ;
Beffield, AJ .
ORGANIC LETTERS, 2003, 5 (26) :5075-5078
[2]   The palladium(II)-catalyzed Nazarov reaction [J].
Bee, C ;
Leclerc, E ;
Tius, MA .
ORGANIC LETTERS, 2003, 5 (26) :4927-4930
[3]   Different lanthanide ions and the pybox substituents induce the reverse of the sense of induction in the enantioselective Diels-Alder reaction between acryloyloxazolidinone and cyclopentadiene [J].
Desimoni, G ;
Faita, G ;
Guala, M ;
Pratelli, C .
JOURNAL OF ORGANIC CHEMISTRY, 2003, 68 (20) :7862-7866
[4]   A catalytic Michael addition of thiols to α,β-unsaturated carbonyl compounds:: Asymmetric Michael additions and asymmetric protonations [J].
Emori, E ;
Arai, T ;
Sasai, H ;
Shibasaki, M .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1998, 120 (16) :4043-4044
[5]   A general method for the enantioselective synthesis of pantolactone derivatives [J].
Evans, DA ;
Wu, J ;
Masse, CE ;
MacMillan, DWC .
ORGANIC LETTERS, 2002, 4 (20) :3379-3382
[6]   C2-symmetric Sc(III)-complexes chiral Lewis acids.: Catalytic enantioselective aldol additions glyoxylate esters [J].
Evans, DA ;
Masse, CE ;
Wu, J .
ORGANIC LETTERS, 2002, 4 (20) :3375-3378
[7]   Highly enantioselective syntheses of homopropargylic alcohols and dihydrofurans catalyzed by a bis(oxazolinyl)pyridine-scandium triflate complex [J].
Evans, DA ;
Sweeney, ZK ;
Rovis, T ;
Tedrow, JS .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2001, 123 (48) :12095-12096
[8]   Enantioselective indole Friedel-Crafts alkylations catalyzed by bis(oxazolinyl)pyridine-scandium(III) triflate complexes [J].
Evans, DA ;
Scheidt, KA ;
Fandrick, KR ;
Lam, HW ;
Wu, J .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (36) :10780-10781
[9]   Ionic hydrogenation of oxyallyl intermediates: the reductive Nazarov cyclization [J].
Giese, S ;
West, FG .
TETRAHEDRON, 2000, 56 (52) :10221-10228
[10]  
Giese S, 2000, ANGEW CHEM INT EDIT, V39, P1970, DOI 10.1002/1521-3773(20000602)39:11<1970::AID-ANIE1970>3.0.CO