Dearomatizing annelation of five-membered rings to naphthalenes by organolithium cyclization

被引：27

作者：

Clayden, J ^{[1
]}

Kenworthy, MN ^{[1
]}

机构：

[1] Univ Manchester, Dept Chem, Manchester M13 9PL, Lancs, England

来源：

ORGANIC LETTERS | 2002年 / 4卷 / 05期

关键词：

D O I：

10.1021/ol0172626

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

[GRAPHICS] gamma-Lithiopropylnaphthalenes and their oxa- and aza-tethered analogues cyclize by nucleophilic addition of the organolithium to the naphthalene ring. The resulting benzyllithiums react stereoselectively with electrophiles to give dearomatized tricyclic products with structural similarity to the aryinaphthalene lignans.

引用

页码：787 / 790

页数：4

共 71 条

[1] Highly selective aziridination of imines using trimethylsilyldiazomethane and applications of C-silylaziridines in synthesis [J].

Aggarwal, VK ;

Ferrara, M .

ORGANIC LETTERS, 2000, 2 (25) :4107-4110

[2] Synthesis of a potent (±)-4-(2-hydroxyphenyl) analogue of the acromelic acids by dearomatising cyclisation of a lithiated N-p-methoxybenzyl-4-methoxy-l-naphthamide [J].

Ahmed, A ;

Bragg, RA ;

Clayden, J ;

Tchabanenko, K .

TETRAHEDRON LETTERS, 2001, 42 (20) :3407-3410

[3] Dearomatising cyclisations of lithiated N-benzylbenzamides [J].

Ahmed, A ;

Clayden, J ;

Yasin, SA .

CHEMICAL COMMUNICATIONS, 1999, (03) :231-232

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

Ahmed, A ;

Clayden, J ;

Rowley, M .

CHEMICAL COMMUNICATIONS, 1998, (03) :297-298

[5] Anion translocation in organolithiums: A mechanism for the lithiation and cyclisation of tertiary naphthamides [J].

Ahmed, A ;

Clayden, J ;

Rowley, M .

TETRAHEDRON LETTERS, 1998, 39 (34) :6103-6106

[6] 1,3,4,5-tetrahydroazepin-2-ones by dearomatising anionic cyclisation of N-allyl-1-naphthamides [J].

Ahmed, A ;

Clayden, J ;

Rowley, M .

SYNLETT, 1999, (12) :1954-1956

[7]

AYRES DC, 1990, LIGNANS CHEM BIOL CL

[8] PREPARATION OF (1-NORBORNYLMETHYL)LITHIUM [J].

BAILEY, WF ;

KHANOLKAR, AD .

ORGANOMETALLICS, 1993, 12 (01) :239-240

[9] Generation and cyclization of a benzyne-tethered alkyllithium: Preparation of 4-substituted indans [J].

Bailey, WF ;

Longstaff, SC .

JOURNAL OF ORGANIC CHEMISTRY, 1998, 63 (03) :432-433

[10] ANIONIC CYCLIZATION OF OLEFINIC ALKYLLITHIUMS - RING-CLOSURE OF TERMINALLY SUBSTITUTED 5-HEXENYLLITHIUMS [J].

BAILEY, WF ;

GAVASKAR, KV .

TETRAHEDRON, 1994, 50 (20) :5957-5970

← 1 2 3 4 5 6 7 8 →