DEVELOPMENT OF A CHIRAL STABILIZED AZOMETHINE YLID - A CHIRAL RELAY SYSTEM

被引：47

作者：

ANSLOW, AS

HARWOOD, LM

PHILLIPS, H

WATKIN, D

机构：

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

[2] UNIV OXFORD,CHEM CRYSTALLOG LAB,OXFORD OX1 3PD,ENGLAND

来源：

TETRAHEDRON-ASYMMETRY | 1991年 / 2卷 / 03期

关键词：

D O I：

10.1016/S0957-4166(00)82350-2

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

The chiral, stabilised azomethine ylid (2) derived from (R)-2-phenylglycinol has been demonstrated to undergo enantioselective 1,3-dipolar cycloaddition reactions with a range of alkene and alkyne dipolarophiles.

引用

页码：169 / 172

页数：4

共 14 条

[1] X=Y-ZH SYSTEMS AS POTENTIAL 1,3-DIPOLES .19. INTRAMOLECULAR CYCLO-ADDITIONS OF NON-STABILIZED AZOMETHINE YLIDES GENERATED VIA THE DECARBOXYLATIVE ROUTE FROM ALPHA-AMINO-ACIDS [J].

ARDILL, H ;

GRIGG, R ;

SRIDHARAN, V ;

SURENDRAKUMAR, S .

TETRAHEDRON, 1988, 44 (15) :4953-4966

[2] METAL-ION CATALYZED ASYMMETRIC 1,3-DIPOLAR CYCLOADDITION REACTIONS OF IMINES OF ALPHA-AMINO ESTERS [J].

BARR, DA ;

DORRITY, MJ ;

GRIGG, R ;

MALONE, JF ;

MONTGOMERY, J ;

RAJVIROONGIT, S ;

STEVENSON, P .

TETRAHEDRON LETTERS, 1990, 31 (45) :6569-6572

[3] X=Y-ZH SYSTEMS AS POTENTIAL 1,3-DIPOLES .15. AMINE GENERATED AZAALLYL ANIONS VERSUS METALLO-1,3-DIPOLES IN CYCLO-ADDITIONS OF ALPHA-AMINO-ACID ESTERS - FACILE REGIO-SPECIFIC AND STEREO-SPECIFIC FORMATION OF PYRROLIDINES [J].

BARR, DA ;

GRIGG, R ;

GUNARATNE, HQN ;

KEMP, J ;

MCMEEKIN, P ;

SRIDHARAN, V .

TETRAHEDRON, 1988, 44 (02) :557-570

[4] TI(IV) MEDIATED TRANS-ESTERIFICATION AND REGIO-SPECIFIC AND STEREO-SPECIFIC CYCLO-ADDITION OF IMINES OF ALPHA-AMINO ESTERS - REVERSAL OF NORMAL REGIOCHEMISTRY [J].

BARR, DA ;

GRIGG, R ;

SRIDHARAN, V .

TETRAHEDRON LETTERS, 1989, 30 (35) :4727-4730

[5] SYNTHESIS OF 2,3-DIHYDRO-6H-1,4-OXAZIN-2-ONES CHIRAL AT C(3) AND ASYMMETRIC INDUCTION IN HYDROGENATION OF AZOMETHINE BOND [J].

CAPLAR, V ;

LISINI, A ;

KAJFEZ, F ;

KOLBAH, D ;

SUNJIC, V .

JOURNAL OF ORGANIC CHEMISTRY, 1978, 43 (07) :1355-1360

[6] ENANTIOSELECTIVE SYNTHESIS OF ALPHA-AMINO-ACID DERIVATIVES VIA THE STEREOSELECTIVE ALKYLATION OF A HOMOCHIRAL GLYCINE ENOLATE SYNTHON [J].

DELLARIA, JF ;

SANTARSIERO, BD .

JOURNAL OF ORGANIC CHEMISTRY, 1989, 54 (16) :3916-3926

[7]

HUSINEC S, 1988, TETRAHEDRON LETT, P6649

[8] 2,5-UNSUBSTITUTED PYRROLIDINES FROM FORMALDEHYDE AND AMINO-ACIDS THROUGH INSITU AZOMETHINE-YLIDE 1,3-DIPOLAR CYCLO-ADDITION TO ALKENES [J].

JOUCLA, M ;

MORTIER, J .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1985, (22) :1566-1567

[9] STUDIES IN SYNTHESIS OF ANTIBIOTICS GLIOTOXIN, SPORIDESMIN, ARANOTIN, AND CHAETOCIN .3. INTRODUCTION OF ALKYL-GROUPS AND SULFUR FUNCTIONS INTO 3-POSITIONS AND 6-POSITIONS OF 2.5-DIOXOPIPERAZINES BY ELECTROPHILIC SUBSTITUTIONS [J].

POISEL, H ;

SCHMIDT, U .

CHEMISCHE BERICHTE-RECUEIL, 1972, 105 (02) :625-&

[10]

ROUDEN J, 1989, TETRAHEDRON LETT, P5133

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