Enantiodiscrimination and enantiocontrol of neutral and cationic PtII complexes bearing the Tropos biphep ligand:: Application to asymmetric Lewis acid catalysis

被引:66
作者
Mikami, K [1 ]
Kakuno, H [1 ]
Aikawa, K [1 ]
机构
[1] Tokyo Inst Technol, Dept Appl Chem, Grad Sch Sci & Engn, Meguro Ku, Tokyo 1528552, Japan
关键词
chirality; Diels-Alder reaction; enantioselectivity; ene reaction; platinum;
D O I
10.1002/anie.200502682
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
(Chemical Equation Presented) The stereochemically stable, enantiopure biphep-Pt complexes can be employed as an atropos asymmetric catalyst at 50°C or below. Both enantiomeric forms of this complex can be obtained by using either the chiral diamine (R)-dabn or its diamide (R)-dabnTf followed by chirally controlled formation of the single biphep-Pt enantiomer at higher (> 60°C) temperatures (see scheme; Tf=trifluoromethanesulfonate). © 2005 Wiley-VCH Verlag GmbH & Co. KGaA.
引用
收藏
页码:7257 / 7260
页数:4
相关论文
共 27 条
[1]   Asymmetric catalysis of ene reactions with trifluoropyruvate catalyzed by dicationic palladium(II) complexes [J].
Aikawa, K ;
Kainuma, S ;
Hatano, M ;
Mikami, K .
TETRAHEDRON LETTERS, 2004, 45 (01) :183-185
[2]  
[Anonymous], 1998, TRANSITION METALS OR
[3]  
[Anonymous], 1993, HDB ENANTIOSELECTIVE
[4]   Asymmetric catalysis with the normally unresolvable, conformationally dynamic 2,2′-bis(diphenylphosphino)-1,1′-biphenyl (biphep) [J].
Becker, JJ ;
White, PS ;
Gagné, MR .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2001, 123 (38) :9478-9479
[5]   The activation barrier to axial torsion in 2,2'-bis(diphenylphosphino)biphenyl [J].
Desponds, O ;
Schlosser, M .
TETRAHEDRON LETTERS, 1996, 37 (01) :47-48
[6]   Highly efficient asymmetric hetero-Diels-Alder reactions of carbonyl compounds catalyzed by Lewis acid platinum complexes of conformationally flexible NUPHOS-type diphosphines [J].
Doherty, S ;
Knight, JG ;
Hardacre, C ;
Lou, HK ;
Newman, CR ;
Rath, RK ;
Campbell, S ;
Nieuwenhuyzen, M .
ORGANOMETALLICS, 2004, 23 (26) :6127-6133
[7]   Highly efficient asymmetric lewis acid catalysis with platinum group complexes of conformationally flexible 1,3-butadiene-bridged diphosphines, NUPHOS [J].
Doherty, S ;
Newman, CR ;
Rath, RK ;
Luo, HK ;
Nieuwenhuyzen, M ;
Knight, JG .
ORGANIC LETTERS, 2003, 5 (21) :3863-3866
[8]  
Jacobsen E. N., 1999, COMPREHENSIVE ASYMME, V1- 3
[9]   Solvent effects in asymmetric hetero Diels-Alder and ene reactions [J].
Johannsen, M ;
Jorgensen, KA .
TETRAHEDRON, 1996, 52 (21) :7321-7328
[10]   ASYMMETRIC HETERO-DIELS-ALDER REACTIONS AND ENE REACTIONS CATALYZED BY CHIRAL COPPER(II) COMPLEXES [J].
JOHANNSEN, M ;
JORGENSEN, KA .
JOURNAL OF ORGANIC CHEMISTRY, 1995, 60 (18) :5757-5762