Remarkably high asymmetric amplification in the chiral lanthanide complex-catalyzed hetero-Diels-Alder reaction:: First example of the nonlinear effect in ML3 system

被引：81

作者：

Furuno, H ^{[1
]}

Hanamoto, T ^{[1
]}

Sugimoto, Y ^{[1
]}

Inanaga, J ^{[1
]}

机构：

[1] Kyushu Univ, Inst Fundamental Res Organ Chem, Higashi Ku, Fukuoka 8128581, Japan

来源：

ORGANIC LETTERS | 2000年 / 2卷 / 01期

关键词：

D O I：

10.1021/ol991189q

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

[GRAPHICS] A remarkably high asymmetric amplification was realized in the Yb[(R)-BNP](3)-catalyzed hetero-Diels-Alder reaction as the first example in the metal/chiral ligand 1:3 system, The mechanism may be explained by the autogenetic formation of the enantiopure complex as the most active catalyst. The enantiomer discriminative formation of homochiral ML3 complexes is quite general within the lanthanide metal ions with similar ionic radii to that of the ytterbium ion.

引用

页码：49 / 52

页数：4

共 31 条

[1] Nonlinear stereochemical effects in asymmetric reactions [J].

Avalos, M ;

Babiano, R ;

Cintas, P ;

Jimenez, JL ;

Palacios, JC .

TETRAHEDRON-ASYMMETRY, 1997, 8 (18) :2997-3017

[2] CHIRAL INDUCTION IN THE CYCLOCONDENSATION OF ALDEHYDES WITH SILOXYDIENES [J].

BEDNARSKI, M ;

MARING, C ;

DANISHEFSKY, S .

TETRAHEDRON LETTERS, 1983, 24 (33) :3451-3454

[3] Mathematical models of nonlinear effects in asymmetric catalysis: New insights based on the role of reaction rate [J].

Blackmond, DG .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1997, 119 (52) :12934-12939

[4] Kinetic implications of nonlinear effects in asymmetric synthesis [J].

Blackmond, DG .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1998, 120 (51) :13349-13353

[5]

BOM C, 1996, ADV ASYMMETRIC CATAL, P9

[6] Nonlinear effects as 'indicators' in the tuning of asymmetric catalysts [J].

Brunel, JM ;

Luukas, TO ;

Kagan, HB .

TETRAHEDRON-ASYMMETRY, 1998, 9 (11) :1941-1946

[7] ENANTIOSELECTIVE MUKAIYAMA-ALDOL AND ALDOL-DIHYDROPYRONE ANNULATION REACTIONS CATALYZED BY A TRYPTOPHAN-DERIVED OXAZABOROLIDINE [J].

COREY, EJ ;

CYWIN, CL ;

ROPER, TD .

TETRAHEDRON LETTERS, 1992, 33 (46) :6907-6910

[8] Catalytic asymmetric addition of ZnPh2 to ketones:: Enantioselective formation of quaternary stereocenters [J].

Dosa, PI ;

Fu, GC .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1998, 120 (02) :445-446

[9] ASYMMETRIC HETERO-DIELS-ALDER REACTION CATALYZED BY STABLE AND EASILY PREPARED CAB CATALYSTS [J].

GAO, QZ ;

ISHIHARA, K ;

MARUYAMA, T ;

MOURI, M ;

YAMAMOTO, H .

TETRAHEDRON, 1994, 50 (04) :979-988

[10] Synthetic studies of antitumor macrolide laulimalide: Enantioselective synthesis of the C-3-C-14 segment by a catalytic hetero Diels-Alder strategy [J].

Ghosh, AK ;

Packiarajan, M ;

Cappiello, J .

TETRAHEDRON LETTERS, 1997, 38 (14) :2427-2430

← 1 2 3 4 →