SEQUENTIAL AND CASCADE 1,3-DIPOLAR CYCLOADDITION PALLADIUM-CATALYZED CARBONYLATION CYCLIZATION REACTIONS - DIASTEREOSPECIFIC AND HOMOCHIRAL PROCESSES

被引:49
作者
GRIGG, R [1 ]
SRIDHARAN, V [1 ]
SUGANTHAN, S [1 ]
BRIDGE, AW [1 ]
机构
[1] RHONE POULENC RORER,DAGENHAM RES CTR,DAGENHAM RM10 7XS,ENGLAND
关键词
D O I
10.1016/0040-4020(94)00956-U
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Combinations of imine --> azomethine ylide --> cycloaddition cascades with Pd(0) catalysed cyclisation-carbonylation forming 5- and 6-membered lactams in sequential reactions are described and both diastereospecific and homochiral examples are provided, The azomethine ylides can be generated either via thermal 1,2-prototropy or metal ion catalysis at ambient temperature. The former sequence has been combined with the Pd(0) catalysed cascade into a one-pot protocol.
引用
收藏
页码:295 / 306
页数:12
相关论文
共 19 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]   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 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
[4]   PALLADIUM-CATALYZED CYCLIZATION-CYCLOPROPANATION AND CYCLIZATION - ANION CAPTURE PROCESSES OF VINYL TRIFLATES [J].
BROWN, A ;
GRIGG, R ;
RAVISHANKAR, T ;
THORNTONPETT, M .
TETRAHEDRON LETTERS, 1994, 35 (17) :2753-2756
[5]   PALLADIUM CATALYZED TANDEM CYCLIZATION-ANION CAPTURE PROCESSES .1. BACKGROUND AND HYDRIDE ION CAPTURE BY ALKYL-PALLADIUM AND PI-ALLYL-PALLADIUM SPECIES [J].
BURNS, B ;
GRIGG, R ;
SANTHAKUMAR, V ;
SRIDHARAN, V ;
STEVENSON, P ;
WORAKUN, T .
TETRAHEDRON, 1992, 48 (35) :7297-7320
[6]   HOMOCHIRAL CYCLOADDUCTS DERIVED FROM SUGAR ALDOXIMES VIA NITRONE INTERMEDIATES [J].
FREDERICKSON, M ;
GRIGG, R ;
REDPATH, J ;
THORNTONPETT, M .
TETRAHEDRON, 1994, 50 (18) :5495-5502
[7]   X = Y-ZH SYSTEMS AS POTENTIAL 1,3-DIPOLES .40. CHIRAL AZOMETHINE YLIDES FROM HOMOCHIRAL CYCLIC ALPHA-AMINO ESTERS - UNUSUAL REGIOSPECIFIC DEPROTONATION OF IMINIUM IONS [J].
GRIGG, R ;
RANKOVIC, Z ;
THORNTONPETT, M ;
SOMASUNDERAM, A .
TETRAHEDRON, 1993, 49 (38) :8679-8690
[8]   CARBON-MONOXIDE AS A ONE-CARBON COMPONENT IN PALLADIUM-CATALYZED CYCLOADDITION REACTIONS [J].
GRIGG, R ;
KHALIL, H ;
LEVETT, P ;
VIRICA, J ;
SRIDHARAN, V .
TETRAHEDRON LETTERS, 1994, 35 (19) :3197-3200
[9]   SEQUENTIAL 1,3-DIPOLAR CYCLOADDITION-PALLADIUM CATALYZED CYCLIZATION - A POWERFUL NEW TACTICAL COMBINATION [J].
GRIGG, R ;
COULTER, T .
TETRAHEDRON LETTERS, 1991, 32 (10) :1359-1362
[10]   X=Y-ZH SYSTEMS AS POTENTIAL 1,3-DIPOLES .39. METALLO-AZOMETHINE YLIDES FROM ALIPHATIC ALDIMINES - FACILE REGIO-SPECIFIC AND STEREO-SPECIFIC CYCLOADDITION REACTIONS [J].
GRIGG, R ;
MONTGOMERY, J ;
SOMASUNDERAM, A .
TETRAHEDRON, 1992, 48 (47) :10431-10442