A highly chemo- and enantio-selective hetero-Diels-Alder reaction catalysed by chiral aluminium complexes

被引：40

作者：

Graven, A ^{[1
]}

Johannsen, M ^{[1
]}

Jorgensen, KA ^{[1
]}

机构：

[1] AARHUS UNIV,DEPT CHEM,DK-8000 AARHUS C,DENMARK

来源：

CHEMICAL COMMUNICATIONS | 1996年 / 20期

关键词：

D O I：

10.1039/cc9960002373

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A new, highly chemo- and enantio-selective catalytic hetero Diels-Alder reaction of conjugated dienes containing allylic C-H bonds with carbonyl compounds has been developed; with the use of (S)-(-)-BINOL-AlMe (BINOL = 1,1'-bi-2-naphthol) as a catalyst, simple conjugated dienes react with glyoxylate esters, giving the (R)-enantiomer of the hetero-Diels-Alder adduct as the major product with up to 97% ee.

引用

收藏

页码：2373 / 2374

页数：2

相关论文

共 34 条

[1] Catalytic asymmetric synthesis of alpha-hydroxy phosphonates using the Al-Li-BINOL complex [J].

Arai, T ;

Bougauchi, M ;

Sasai, H ;

Shibasaki, M .

JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (09) :2926-2927

[2]

ARAI T, 1996, ANGEW CHEM, V108, P103

[3] VAULTED BIARYLS AS CHIRAL LIGANDS FOR ASYMMETRIC CATALYTIC DIELS-ALDER REACTIONS [J].

BAO, JM ;

WULFF, WD ;

RHEINGOLD, AL .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1993, 115 (09) :3814-3815

[4]

Boger D. L., 1987, HETERO DIELS ALDER M

[5] ASYMMETRIC DIELS-ALDER REACTIONS OF CYCLOPENTADIENE WITH N-CROTONOYL AND N-ACRYLOYL-4,4-DIMETHYL-1,3-OXAZOLIDIN-2-ONE, MEDIATED BY CHIRAL LEWIS-ACIDS [J].

CHAPUIS, C ;

JURCZAK, J .

HELVETICA CHIMICA ACTA, 1987, 70 (02) :436-440

[6] 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

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

GAO, QZ ;

MARUYAMA, T ;

MOURI, M ;

YAMAMOTO, H .

JOURNAL OF ORGANIC CHEMISTRY, 1992, 57 (07) :1951-1952

[8] Solvent effects in asymmetric hetero Diels-Alder and ene reactions [J].

Johannsen, M ;

Jorgensen, KA .

TETRAHEDRON, 1996, 52 (21) :7321-7328

[9] 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

[10] STEREOCHEMISTRY OF DIELS-ALDER REACTIONS AT HIGH-PRESSURE .4. ASYMMETRIC INDUCTION IN HIGH-PRESSURE CYCLOADDITIONS OF (R)-(-)-MENTHYL GLYOXYLATE AND SYMMETRIC 1,3-DIENES [J].

JURCZAK, J ;

TKACZ, M .

JOURNAL OF ORGANIC CHEMISTRY, 1979, 44 (19) :3347-3352

← 1 2 3 4 →