A novel synthesis of 2,5-dihydropyrrole derivatives as enantiomerically enriched building blocks

被引：13

作者：

Cinquin, C ^{[1
]}

Bortolussi, M ^{[1
]}

Bloch, R ^{[1
]}

机构：

[1] UNIV PARIS 11,INST CHIM MOLEC ORSAY,CNRS,LAB CARBOCYCLES,F-91405 ORSAY,FRANCE

来源：

TETRAHEDRON | 1996年 / 52卷 / 20期

关键词：

D O I：

10.1016/0040-4020(96)00323-7

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A general synthesis of optically active 2,5-dihydropyrroles (3-pyrrolines) substituted at the 2-position by a functionalized chain is described. A highly stereoselective intramolecular Michael reaction afforded the five-membered nitrogen rings with an excellent enantiomeric purity. The unsaturation was generated by a retro Diels-Alder reaction. Copyright (C) 1996 Elsevier Science Ltd

引用

页码：6943 / 6952

页数：10

共 38 条

[1] ASYMMETRIC-SYNTHESIS .13. SYNTHESIS OF 2-ALKYLPYRROLIDINES - TOWARDS AZABICYCLIC SYSTEMS [J].

ARSENIYADIS, S ;

HUANG, PQ ;

HUSSON, HP .

TETRAHEDRON LETTERS, 1988, 29 (06) :631-634

[2] COMPLEX-INDUCED PROXIMITY EFFECTS - ENANTIOSELECTIVE SYNTHESES BASED ON ASYMMETRIC DEPROTONATIONS OF N-BOC-PYRROLIDINES [J].

BEAK, P ;

KERRICK, ST ;

WU, SD ;

CHU, JX .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1994, 116 (08) :3231-3239

[3] ASYMMETRIC-SYNTHESIS OF 3S,4R-DIHYDROXYPYRROLIDINES BY REGIOSELECTIVE AND STEREOSELECTIVE HYDROXYLATION OF 4-OXOPROLINE ENOLATE [J].

BLANCO, MJ ;

SARDINA, FJ .

TETRAHEDRON LETTERS, 1994, 35 (45) :8493-8496

[4] STEREOCONTROLLED REACTIONS INDUCED BY A THERMOLABILE GROUP - SYNTHESIS OF OPTICALLY-ACTIVE 1,3-DIOLS [J].

BLOCH, R ;

BORTOLUSSI, M ;

GIRARD, C ;

SECK, M .

TETRAHEDRON, 1992, 48 (03) :453-462

[5] OPTICALLY-ACTIVE 5-MEMBERED OXYGEN-CONTAINING RINGS - A SYNTHESIS OF (+)-ELDANOLIDE [J].

BLOCH, R ;

SECK, M .

TETRAHEDRON, 1989, 45 (12) :3731-3740

[6] TOTAL ASYMMETRIC SYNTHESES OF 1,5-DIDEOXY-1,5-IMINOOCTITOLS AND 1,2,6,7,8-PENTAHYDROXYINDOLIZIDINES [J].

CHEN, YW ;

VOGEL, P .

JOURNAL OF ORGANIC CHEMISTRY, 1994, 59 (09) :2487-2496

[7]

CINQUIN C, 1995, SYNLETT, P339

[8]

COLLADO I, 1994, TETRAHEDRON LETT, V35, P8037

[9] ENANTIOSELECTIVE SYNTHESIS OF 2-SUBSTITUTED PYRROLIDINES FROM 4-HYDROXYNITRILES - APPLICATION TO THE SYNTHESIS OF THE DOPAMINE AGONIST RS-59022 [J].

GOODING, OW ;

BANSAL, RP .

SYNTHETIC COMMUNICATIONS, 1995, 25 (08) :1155-1166

[10] A CONCISE DIASTEREOSELECTIVE SYNTHESIS OF THE NATURAL (2R,3S)-2-HYDROXYMETHYL-3-HYDROXY-PYRROLIDINE [J].

GRIFFARTBRUNET, D ;

LANGLOIS, N .

TETRAHEDRON LETTERS, 1994, 35 (01) :119-122

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