Anionic cyclisations of an N-benzyl naphthamide:: a route to benzo[e]isoindolones

被引:65
作者
Ahmed, A
Clayden, J
Rowley, M
机构
[1] Univ Manchester, Dept Chem, Manchester M13 9PL, Lancs, England
[2] Merck Sharp & Dohme Ltd, Neurosci Res Ctr, Harlow CM20 2QR, Essex, England
关键词
D O I
10.1039/a707683e
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
On treatment with (BuLi)-Li-t and HMPA, N-tert-butyl-N-benzyl-1-naphthamide undergoes cyclisation to a tricyclic enolate which reacts diastereoselectively with electrophiles to give substituted 2,3,3a,9b-tetrahydro-1H-benzo[e]isoindol-1-ones, the first example of an anionic cyclisation onto an aromatic ring.
引用
收藏
页码:297 / 298
页数:2
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共 55 条
[31]   Anionic cyclizations of chiral 2,3-dihydro-4-pyridones: A five-step, asymmetric synthesis of indolizidine 209D [J].
Comins, DL ;
Zhang, YM .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1996, 118 (48) :12248-12249
[32]   Ortho versus adjacent-benzylic directed lithiations of substituted N,N-diethylbenzamides [J].
Court, JJ ;
Hlasta, DJ .
TETRAHEDRON LETTERS, 1996, 37 (09) :1335-1338
[33]   SUBSTITUTION ALPHA TO NITROGEN IN DIBENZYLAMINE VIA CARBANION INTERMEDIATES [J].
FRASER, RR ;
BOUSSARD, G ;
POSTESCU, ID ;
WHITING, JJ ;
WIGFIELD, YY .
CANADIAN JOURNAL OF CHEMISTRY-REVUE CANADIENNE DE CHIMIE, 1973, 51 (07) :1109-1115
[34]   Synthesis of 3-aminopyrrolidin-2-ones by an intramolecular reaction of aziridinecarboxamides. [J].
Funaki, I ;
Thijs, L ;
Zwanenburg, B .
TETRAHEDRON, 1996, 52 (29) :9909-9924
[35]   COMPLEX-INDUCED PROXIMITY EFFECTS AND DIPOLE-STABILIZED CARBANIONS - KINETIC EVIDENCE FOR THE ROLE OF COMPLEXES IN THE ALPHA'-LITHIATIONS OF CARBOXAMIDES [J].
HAY, DR ;
SONG, ZG ;
SMITH, SG ;
BEAK, P .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1988, 110 (24) :8145-8153
[36]   ASYMMETRIC-SYNTHESIS OF THE KEY INTERMEDIATES LEADING TO (-)-APHANORPHINE AND (-)-EPTAZOCINE [J].
HULME, AN ;
HENRY, SS ;
MEYERS, AI .
JOURNAL OF ORGANIC CHEMISTRY, 1995, 60 (05) :1265-1270
[37]   omega-alkenyl-alpha-methoxy-benzyllithiums: Original synthesis and reactivity [J].
Krief, A ;
Bousbaa, J .
TETRAHEDRON LETTERS, 1997, 38 (35) :6291-6294
[38]   SYNTHESIS OF ARYLCYCLOALKANES FROM OMEGA-ALKENYL BENZYLSELENIDES [J].
KRIEF, A ;
KENDA, B ;
BARBEAUX, P ;
GUITTET, E .
TETRAHEDRON, 1994, 50 (24) :7177-7192
[39]   A NEW STRATEGY TO BICYCLO[5.3.0]DECENES VIA ANIONIC INTRAMOLECULAR RING-OPENING OF OXABICYCLO[3.2.1] COMPOUNDS [J].
LAUTENS, M ;
KUMANOVIC, S .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1995, 117 (07) :1954-1964
[40]   UNPRECEDENTED NUCLEOPHILIC-ADDITION OF ORGANOLITHIUMS TO AROMATIC-ALDEHYDES AND KETONES BY COMPLEXATION WITH ALUMINUM TRIS(2,6-DIPHENYLPHENOXIDE) [J].
MARUOKA, K ;
ITO, M ;
YAMAMOTO, H .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1995, 117 (35) :9091-9092