Synthesis and enantioselective Diels-Alder reactions of optically active cobalt(III) salen-1,3-butadien-2-yl complexes

被引：13

作者：

Chapman, JJ

Day, CS

Welker, ME

机构：

[1] Wake Forest Univ, Dept Chem, Winston Salem, NC 27109 USA

[2] Lorillard Res Ctr, Greensboro, NC 27420 USA

来源：

ORGANOMETALLICS | 2000年 / 19卷 / 09期

关键词：

D O I：

10.1021/om000074j

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

The syntheses of two optically active Co(salen)-1,3-butadien-2-yl complexes are reported. One of the dienyl complexes was characterized by X-ray crystallography. The dienyl complexes underwent Diels-Alder reactions with high enantioselectivity with dimethyl fumarate. A highlight of this chemistry is that Diels-Alder cycloadduct cobalt complexes were cleanly cleaved at the cobalt-carbon bond with concomitant optically active cobalt complex starting material and optically active cyclohexene cycloadduct recovery.

引用

收藏

页码：1615 / 1618

页数：4

相关论文

共 30 条

[1] Polymer-supported chiral Co(salen) complexes: Synthetic applications and mechanistic investigations in the hydrolytic kinetic resolution of terminal epoxides [J].

Annis, DA ;

Jacobsen, EN .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1999, 121 (17) :4147-4154

[2] Synthesis and asymmetric Diels-Alder reactions of enantiopure 3-(alkylsulfinyl)-1-methoxy-1,3-butadienes [J].

Aversa, MC ;

Barattucci, A ;

Bonaccorsi, P ;

Giannetto, P ;

JOnes, DN .

JOURNAL OF ORGANIC CHEMISTRY, 1997, 62 (13) :4376-4384

[3]

Backer HJ, 1942, RECL TRAV CHIM PAY-B, V61, P785

[4] Cycloaddition reactions of chiral 2-amino-1,3-butadienes with nitroalkenes: Synthesis of enantiomerically pure 4-nitrocyclohexanones [J].

Barluenga, J ;

Aznar, F ;

Ribas, C ;

Valdes, C .

JOURNAL OF ORGANIC CHEMISTRY, 1997, 62 (20) :6746-6753

[5] Cyclic BF2 adducts of functionalized fischer vinylcarbene complexes:: Preparation and stereoselective Diels-Alder reactions with 2-amino 1,3-dienes [J].

Barluenga, J ;

Canteli, RM ;

Florez, J ;

Garcia-Granda, S ;

Gutierrez-Rodriguez, A ;

Martin, E .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1998, 120 (11) :2514-2522

[6]

BRANDSMA L, 1981, SYNTHESIS ACETYLENES, P65

[7] A new chiral ligand for the Fe-Lewis acid catalysed asymmetric Diels-Alder reaction [J].

Bruin, ME ;

Kundig, EP .

CHEMICAL COMMUNICATIONS, 1998, (23) :2635-2636

[8] Preparation of (L)(N,N'-ethylenebis(salicylideneaminato))-(1,3-butadien-2-yl)cobalt(III) complexes and their utilization in facile and regioselective Diels-Alder reactions [J].

Chapman, JJ ;

Welker, ME .

ORGANOMETALLICS, 1997, 16 (04) :747-755

[9] ENANTIOSELECTIVE TOTAL SYNTHESIS OF BILOBALIDE, A C15 GINKGOLIDE [J].

COREY, EJ ;

SU, WG .

TETRAHEDRON LETTERS, 1988, 29 (28) :3423-3426

[10]

Corey EJ, 1998, ANGEW CHEM INT EDIT, V37, P388, DOI 10.1002/(SICI)1521-3773(19980302)37:4<388::AID-ANIE388>3.0.CO