Diastereoselective synthesis of alpha alpha-disubstituted gamma-carboxypyroglutamates via Sm(III)-azomethine ylide cycloadditions

被引：36

作者：

AlvarezIbarra, C

Csaky, AG

deSilanes, IL

Quiroga, ML

机构：

[1] Depto. de Quim. Orgánica I, Facultad de Química, Universidad Complutense

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1997年 / 62卷 / 03期

关键词：

D O I：

10.1021/jo961418b

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Sm(III)-azomethine ylides 2 have been generated from ketones 1. Cycloaddition of ylides 2 with alpha,beta-unsaturated esters 3 through a transition state chelation-controlled by the metal allowed for the asymmetric synthesis of gamma-carboxypyroglutamates having a quaternary alpha-carbon that are potentially useful in the synthesis of neuroprotective agents.

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页码：479 / 484

页数：6

相关论文

共 63 条

[1] CHIRAL CO(II) AND MN(II) CATALYSTS FOR THE 1,3-DIPOLAR CYCLOADDITION REACTIONS OF AZOMETHINE YLIDES DERIVED FROM ARYLIDENE IMINES OF GLYCINE [J].

ALLWAY, P ;

GRIGG, R .

TETRAHEDRON LETTERS, 1991, 32 (41) :5817-5820

[2] CONFORMATIONAL STUDIES ON PEPTIDES CONTAINING ENANTIOMERIC ALPHA-METHYL ALPHA-AMINO-ACIDS .1. DIFFERENTIAL CONFORMATIONAL PROPERTIES OF (R)-2-METHYLASPARTIC AND (S)-2-METHYLASPARTIC ACID [J].

ALTMANN, KH ;

ALTMANN, E ;

MUTTER, M .

HELVETICA CHIMICA ACTA, 1992, 75 (04) :1198-1210

[3] DIASTEREOSELECTIVE SYNTHESIS OF SUBSTITUTED GLUTAMIC-ACID DERIVATIVES VIA MICHAEL ADDITIONS OF N-[BIS(METHYLTHIO)METHYLENE]GLYCINATES UNDER SOLID-LIQUID PHASE-TRANSFER CATALYSIS [J].

ALVAREZIBARRA, C ;

CSAKY, AG ;

MAROTO, M ;

QUIROGA, ML .

JOURNAL OF ORGANIC CHEMISTRY, 1995, 60 (21) :6700-6705

[4] DIASTEREOSELECTIVE SYNTHESIS OF FUNCTIONALIZED 2,4-DIAMINO-3-HYDROXYGLUTARIC ACID-DERIVATIVES OF POTENTIAL BIOLOGICAL INTEREST FROM GLYCINE DERIVATIVES [J].

ALVAREZIBARRA, C ;

DOMINGUEZFERNANDEZ, C ;

CSAKY, AG ;

MARTINEZSANTOS, E ;

QUIROGA, ML ;

GUTIERREZ, E .

TETRAHEDRON LETTERS, 1993, 34 (34) :5463-5466

[5]

ANUNZIATA R, 1991, TETRAHEDRON-ASYMMETR, V2, P1329

[6] RECENT ADVANCES IN ASYMMETRIC-SYNTHESIS .2. [J].

APSIMON, JW ;

COLLIER, TL .

TETRAHEDRON, 1986, 42 (19) :5157-5254

[7] STEREOCONTROLLED 5-EXO-TRIG CYCLIZATION OF IMIDOYL RADICALS IN THE SYNTHESIS OF SUBSTITUTED (ALKYLTHIO)PYRROLINES, PYROGLUTAMATES, AND THIOPYROGLUTAMATES [J].

BACHI, MD ;

MELMAN, A .

JOURNAL OF ORGANIC CHEMISTRY, 1995, 60 (19) :6242-6244

[8]

Bachi MD, 1996, SYNLETT, P60

[9] X=Y-ZH COMPOUNDS AS POTENTIAL 1,3-DIPOLES .43. METAL-ION CATALYZED ASYMMETRIC 1,3-DIPOLAR CYCLOADDITION REACTIONS OF IMINES AND MENTHYL ACRYLATE [J].

BARR, DA ;

DORRITY, MJ ;

GRIGG, R ;

HARGREAVES, S ;

MALONE, JF ;

MONTGOMERY, J ;

REDPATH, J ;

STEVENSON, P ;

THORNTONPETT, M .

TETRAHEDRON, 1995, 51 (01) :273-294

[10] ENANTIOMERICALLY ENRICHED ALPHA-METHYL AMINO-ACIDS - USE OF AN ACYCLIC, CHIRAL ALANINE-DERIVED DIANION WITH A HIGH DIASTEREOFACIAL BIAS [J].

BERKOWITZ, DB ;

SMITH, MK .

JOURNAL OF ORGANIC CHEMISTRY, 1995, 60 (05) :1233-1238

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