Functionalised pyrrolidinones derived from (S)-pyroglutamic acid

被引：46

作者：

Beard, MJ

Bailey, JH

Cherry, DT

Moloney, MG

Shim, SB

Statham, KA

Bamford, MJ

Lamont, RB

机构：

[1] UNIV OXFORD,DYSON PERRINS LAB,OXFORD OX1 3QY,ENGLAND

[2] GLAXO WELLCOME,MED RES CTR,STEVENAGE SG1 2NY,HERTS,ENGLAND

来源：

TETRAHEDRON | 1996年 / 52卷 / 10期

关键词：

D O I：

10.1016/0040-4020(96)00047-6

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The generation of the lactam enolate derived from bicyclic lactams 2a-c, prepared from (S)-pyroglutamic acid 1a, and subsequent reaction with a range of electrophiles, is reported. Exo-diastereoselectivity is generally favoured. The deprotection of some of these adducts to give functionalised hydroxymethylpyrrolidinones is readily achieved by simple hemiaminal ether cleavage under acidic conditions.

引用

收藏

页码：3719 / 3740

页数：22

相关论文

共 39 条

[1] APPROACHES TO THE SYNTHESIS OF CYTOCHALASANS .9. A VERSATILE CONCEPT LEADING TO ALL STRUCTURAL TYPES OF CYTOCHALASANS [J].

ACKERMANN, J ;

MATTHES, M ;

TAMM, C .

HELVETICA CHIMICA ACTA, 1990, 73 (01) :122-132

[2] STEREOSELECTIVE METHYLATIONS OF BICYCLIC LACTAMS DERIVED FROM PYROGLUTAMIC ACID [J].

ARMSTRONG, RW ;

DEMATTEI, JA .

TETRAHEDRON LETTERS, 1991, 32 (41) :5749-5752

[3] (L)-PYROGLUTAMIC ACID AS A CHIRAL STARTING MATERIAL FOR ASYMMETRIC-SYNTHESIS [J].

BALDWIN, JE ;

MOLONEY, MG ;

SHIM, SB .

TETRAHEDRON LETTERS, 1991, 32 (10) :1379-1380

[4]

BAMFORD M, 1995, TETRAHEDRON-ASYMMETR, P337

[5] STEREOSELECTIVE ADDITION OF GRIGNARD-DERIVED ORGANOCOPPER REAGENTS TO N-ACYLIMINIUM IONS - SYNTHESIS OF ENANTIOPURE 5-SUBSTITUTED AND 4,5-SUBSTITUTED PROLINATES [J].

COLLADO, I ;

EZQUERRA, J ;

PEDREGAL, C .

JOURNAL OF ORGANIC CHEMISTRY, 1995, 60 (16) :5011-5015

[6] ALDOL REACTIONS OF PYROGLUTAMATES - CHIRAL SYNTHESIS OF 4-ALPHA(S)-(ARYLMETHYL)PYROGLUTAMATES AND 4-BETA(R)-(ARYLMETHYL)PYROGLUTAMATES [J].

DIKSHIT, DK ;

PANDAY, SK .

JOURNAL OF ORGANIC CHEMISTRY, 1992, 57 (06) :1920-1924

[7] ENANTIOCONTROL AND REGIOCONTROL IN LACTAM SYNTHESES BY INTRAMOLECULAR CARBON-HYDROGEN INSERTION REACTIONS OF DIAZOACETAMIDES CATALYZED BY CHIRAL RHODIUM(II) CARBOXAMIDES [J].

DOYLE, MP ;

PROTOPOPOVA, MN ;

WINCHESTER, WR ;

DANIEL, KL .

TETRAHEDRON LETTERS, 1992, 33 (51) :7819-7822

[8] STEREOSELECTIVE DOUBLE ALKYLATION OF ETHYL N-BOC-PYROGLUTAMATE [J].

EZQUERRA, J ;

PEDREGAL, C ;

RUBIO, A ;

VAQUERO, JJ ;

MATIA, MP ;

MARTIN, J ;

DIAZ, A ;

NAVIO, JLG ;

DEETER, JB .

JOURNAL OF ORGANIC CHEMISTRY, 1994, 59 (15) :4327-4331

[9] DIASTEREOSELECTIVITY IN THE PREPARATION OF BETA-SILYLESTERS FROM ALPHA-BETA-UNSATURATED ESTERS AND AMIDES ATTACHED TO CHIRAL AUXILIARIES [J].

FLEMING, I ;

KINDON, ND .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1987, (15) :1177-1179

[10] CHIRAL COPPER SEMICORRIN COMPLEXES AS ENANTIOSELECTIVE CATALYSTS FOR THE CYCLOPROPANATION OF OLEFINS BY DIAZO-COMPOUNDS [J].

FRITSCHI, H ;

LEUTENEGGER, U ;

PFALTZ, A .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1986, 25 (11) :1005-1006

← 1 2 3 4 →