C2-symmetric bissulfoximines as ligands in copper-catalyzed enantioselective Diels-Alder reactions

被引:78
作者
Bolm, C [1 ]
Martin, M [1 ]
Simic, O [1 ]
Verrucci, M [1 ]
机构
[1] Rhein Westfal TH Aachen, Inst Organ Chem, D-52056 Aachen, Germany
关键词
D O I
10.1021/ol027273e
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
[GRAPHICS] Bissulfoximines have been used as chiral ligands in copper-catalyzed enantioselective Diels-Alder reactions between acryloyl-2-oxazolidinones and cyclopentadiene. After optimizing the ligand structure, the metal source, the counterions, and the solvent, products with up to 93% ee have been obtained.
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收藏
页码:427 / 429
页数:3
相关论文
共 34 条
[1]  
[Anonymous], 1998, TRANSITION METALS OR
[2]  
[Anonymous], ANGEW CHEM
[3]   ENANTIOSELECTIVE TRIMETHYLSILYLCYANATION OF ALDEHYDES [J].
BOLM, C ;
MULLER, P .
TETRAHEDRON LETTERS, 1995, 36 (10) :1625-1628
[4]  
Bolm C, 2002, SYNTHESIS-STUTTGART, P879
[5]  
Bolm C, 2001, SYNLETT, P1878
[6]   Highly enantioselective hetero-Diels-Alder reactions catalyzed by a C2-symmetric bis(sulfoximine) Copper(II) complex [J].
Bolm, C ;
Simic, O .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2001, 123 (16) :3830-3831
[7]   BIS(4,5-DIHYDROOXAZOLYL) DERIVATIVES IN ASYMMETRIC CATALYSIS [J].
BOLM, C .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1991, 30 (05) :542-543
[8]  
Bolm C, 1996, SYNLETT, P775
[9]   Sulfoximine-titanium reagents in enantioselective trimethylsilylcyanations of aldehydes [J].
Bolm, C ;
Muller, P ;
Harms, K .
ACTA CHEMICA SCANDINAVICA, 1996, 50 (04) :305-315
[10]   Optically active sulfoximines in enantioselective palladium catalysis [J].
Bolm, C ;
Kaufmann, D ;
Zehnder, M ;
Neuburger, M .
TETRAHEDRON LETTERS, 1996, 37 (23) :3985-3988