THE SYNTHESIS OF BRIDGED-RING CARBOCYCLES AND HETEROCYCLES VIA PALLADIUM CATALYZED REGIOSPECIFIC CYCLIZATION REACTIONS

被引：60

作者：

GRIGG, R ^{[1
]}

SANTHAKUMAR, V ^{[1
]}

SRIDHARAN, V ^{[1
]}

STEVENSON, P ^{[1
]}

TEASDALE, A ^{[1
]}

THORNTONPETT, M ^{[1
]}

WORAKUN, T ^{[1
]}

机构：

[1] QUEENS UNIV BELFAST,DEPT CHEM,BELFAST BT9 5AG,ANTRIM,NORTH IRELAND

来源：

TETRAHEDRON | 1991年 / 47卷 / 46期

关键词：

PALLADIUM CATALYSIS; BRIDGED-RING CYCLIZATION;

D O I：

10.1016/S0040-4020(01)91034-8

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A catalyst system comprising 10 mol % (Pd(OAc) and 20 mol % PPh3 effects the cyclisation of aryl halides onto proximate alkenes via 5-, 6-, and 7-exo-trig, and 7-endo-trig processes giving a variety of bridged-ring carbo- and hetero-cycles in excellent yield. Double bond isomerisation in the product is rarely encountered and may be suppressed by the addition of Tl(1) salts. One example of diastereospecific bis-cyclisation is given and the crystal structure of 1-aza-2-sulphonyl-3,4-benzobicyclo[3.2.1]nona-6-ene is reported.

引用

页码：9703 / 9720

页数：18

共 41 条

[1] PALLADIUM-CATALYZED POLYENE CYCLIZATIONS OF DIENYL ARYL IODIDES [J].

ABELMAN, MM ;

OVERMAN, LE .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1988, 110 (07) :2328-2329

[2] INTRAMOLECULAR ALKENE ARYLATIONS FOR RAPID ASSEMBLY OF POLYCYCLIC SYSTEMS CONTAINING QUATERNARY CENTERS - A NEW SYNTHESIS OF SPIROOXINDOLES AND OTHER FUSED AND BRIDGED RING-SYSTEMS [J].

ABELMAN, MM ;

OH, T ;

OVERMAN, LE .

JOURNAL OF ORGANIC CHEMISTRY, 1987, 52 (18) :4130-4133

[3] CONSTRUCTION OF QUATERNARY CARBON CENTERS BY PALLADIUM-CATALYZED INTRAMOLECULAR ALKENE INSERTIONS - TOTAL SYNTHESIS OF THE AMARYLLIDACEAE ALKALOIDS (+/-)-TAZETTINE AND (+/-)-6A-EPIPRETAZETTINE [J].

ABELMAN, MM ;

OVERMAN, LE ;

TRAN, VD .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1990, 112 (19) :6959-6964

[4] TRANSITION-METAL-ASSISTED ASYMMETRIC-SYNTHESIS OF AMINO-ACID-ANALOGS - A NEW SYNTHESIS OF OPTICALLY PURE D-PYRIDYLALANINE AND L-PYRIDYLALANINE [J].

BOZELL, JJ ;

VOGT, CE ;

GOZUM, J .

JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (07) :2584-2587

[5] PALLADIUM-CATALYZED ALPHA-ARYLATION OF VINYL BUTYL ETHER WITH ARYL HALIDES [J].

CABRI, W ;

CANDIANI, I ;

BEDESCHI, A ;

SANTI, R .

TETRAHEDRON LETTERS, 1991, 32 (14) :1753-1756

[6] PALLADIUM-CATALYZED POLYENE CYCLIZATIONS OF TRIENYL TRIFLATES [J].

CARPENTER, NE ;

KUCERA, DJ ;

OVERMAN, LE .

JOURNAL OF ORGANIC CHEMISTRY, 1989, 54 (25) :5846-5848

[7] EVIDENCE THAT PALLADIUM(0)-PROMOTED CYCLIZATIONS OF UNSATURATED ALPHA-IODOCARBONYLS OCCUR BY AN ATOM TRANSFER MECHANISM [J].

CURRAN, DP ;

CHANG, CT .

TETRAHEDRON LETTERS, 1990, 31 (07) :933-936

[8] SUPPRESSION OF ALKENE ISOMERIZATION IN PRODUCTS FROM INTRAMOLECULAR HECK REACTIONS BY ADDITION OF TL(I) SALTS [J].

GRIGG, R ;

LOGANATHAN, V ;

SANTHAKUMAR, V ;

SRIDHARAN, V ;

TEASDALE, A .

TETRAHEDRON LETTERS, 1991, 32 (05) :687-690

[9] PALLADIUM-CATALYZED AND RHODIUM-CATALYZED CYCLIZATION OF 1,6-DIENES, 1,7-DIENES AND 1,8-DIENES TO CYCLOPENTENES AND METHYLENECYCLOPENTENES - CRYSTAL-STRUCTURE OF DICHLORO(4,4-DIACETYLHEPTA-1,6-DIENE)PLATINUM(II) [J].

GRIGG, R ;

MALONE, JF ;

MITCHELL, TRB ;

RAMASUBBU, A ;

SCOTT, RM .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1984, (08) :1745-1754

[10] PALLADIUM CATALYZED TANDEM CYCLIZATION-ANION CAPTURE PROCESSES INITIATED BY ALKYL-PALLADIUM AND PI-ALLYL-PALLADIUM SPECIES [J].

GRIGG, R ;

SUKIRTHALINGAM, S ;

SRIDHARAN, V .

TETRAHEDRON LETTERS, 1991, 32 (22) :2545-2548

← 1 2 3 4 5 →