Stereocontrolled 1,3-dipolar cycloadditions using Oppolzer's camphor sultam as the chiral auxiliary for carbonyl stabilized azomethine ylides

被引：43

作者：

Garner, P ^{[1
]}

Dogan, Ö ^{[1
]}

Youngs, WJ ^{[1
]}

Kennedy, VO ^{[1
]}

Protasiewicz, J ^{[1
]}

Zaniewski, R ^{[1
]}

机构：

[1] Case Western Reserve Univ, Dept Chem, Cleveland, OH 44106 USA

来源：

TETRAHEDRON | 2001年 / 57卷 / 01期

关键词：

cycloadditions; pyrrolidines; stereocontrol; sultams;

D O I：

10.1016/S0040-4020(00)00998-4

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Two complementary approaches to substituted pyrrolidines via stereocontrolled 1,3-dipolar cycloaddition reactions of chiral azomethine ylides are described. In one approach, chiral azomethine ylides were generated by thermolysis of aziridine carboxylate sultams and trapped with a variety of dipolarophiles to give good yields of the corresponding cycloadducts. In the second approach, chiral azomethine ylides were generated from glycyl sultams by 'imine tautomerization' and trapped with dipolarophiles to give good yields of the corresponding cycloadducts, (C) 2000 Elsevier Science Ltd. All rights reserved.

引用

页码：71 / 85

页数：15

共 45 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]

[Anonymous], 1984, 1,3-Dipolar Cycloaddition Chemistry

[3]

[Anonymous], 1989, Adv. Heterocycl. Chem, DOI DOI 10.1016/S0065-2725(08)60332-3

[4] DEVELOPMENT OF CHIRAL STABILIZED AZOMETHINE YLIDES - A CHIRAL MEMORY RELAY SYSTEM [J].

ANSLOW, AS ;

HARWOOD, LM ;

PHILLIPS, H ;

WATKIN, D ;

WONG, LF .

TETRAHEDRON-ASYMMETRY, 1991, 2 (12) :1343-1358

[5]

BALDWIN JE, 1994, SYNLETT, P925

[6] STUDY OF THE REGIOCHEMISTRY AND STEREOCHEMISTRY OF THE [3 + 2] CYCLO-ADDITION BETWEEN NONSTABILIZED AZOMETHINE YLIDES GENERATED FROM TERTIARY AMINE N-OXIDES AND VARIOUS DIPOLAROPHILES [J].

CHASTANET, J ;

ROUSSI, G .

JOURNAL OF ORGANIC CHEMISTRY, 1988, 53 (16) :3808-3812

[7] A new stereoselective approach to the manzamine alkaloids [J].

Coldham, I ;

Coles, SJ ;

Crapnell, KM ;

Fernández, JC ;

Haxell, TFN ;

Hursthouse, MB ;

Moseley, JD ;

Treacy, AB .

CHEMICAL COMMUNICATIONS, 1999, (17) :1757-1758

[8] THE STABILIZED IMINIUM YLIDE OLEFIN [3 + 2] CYCLOADDITION REACTION - TOTAL SYNTHESIS OF SCELETIUM ALKALOID-A4 [J].

CONFALONE, PN ;

HUIE, EM .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1984, 106 (23) :7175-7178

[9] CLEAVAGE OF N-ACYL OXAZOLIDONES [J].

DAMON, RE ;

COPPOLA, GM .

TETRAHEDRON LETTERS, 1990, 31 (20) :2849-2852

[10] CHEMISTRY OF OXAZIRIDINES .18. SYNTHESIS AND ENANTIOSELECTIVE OXIDATIONS OF THE [(8,8-DIHALOCAMPHORYL)SULFONYL]OXAZIRIDINES [J].

DAVIS, FA ;

WEISMILLER, MC ;

MURPHY, CK ;

REDDY, RT ;

CHEN, BC .

JOURNAL OF ORGANIC CHEMISTRY, 1992, 57 (26) :7274-7285

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