Asymmetric deprotonation and dearomatising cyclisation of N-benzyl benzamides using chiral lithium amides:: formal synthesis of (-)-kainic acid

被引：51

作者：

Clayden, J

Menet, CJ

Mansfield, DJ

机构：

[1] Univ Manchester, Dept Chem, Manchester M20 5LG, Lancs, England

[2] Aventis CropSci SA, Ctr Rech Dargoire, F-69263 Lyon 09, France

来源：

CHEMICAL COMMUNICATIONS | 2002年 / 01期

关键词：

D O I：

10.1039/b109188c

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Chiral lithium amides deprotonate N-benzyl benzamides enantioselectively, initiating an asymmetric dearomatising cyclisation to enantiomerically enriched isoindolinones.

引用

页码：38 / 39

页数：2

共 23 条

[1] 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

[2] Barriers to rotation about the chiral axis of tertiary aromatic amides [J].

Ahmed, A ;

Bragg, RA ;

Clayden, J ;

Lai, LW ;

McCarthy, C ;

Pink, JH ;

Westlund, N ;

Yasin, SA .

TETRAHEDRON, 1998, 54 (43) :13277-13294

[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] Complex-induced proximity effects in directed lithiations: Analysis of intra- and intermolecular kinetic isotope effects in directed aryl and benzylic lithiations [J].

Anderson, DR ;

Faibish, NC ;

Beak, P .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1999, 121 (33) :7553-7558

[6] Rapid access to N-Boc phenylglycine derivatives via benzylic lithiation reactions [J].

Barberis, C ;

Voyer, N ;

Roby, J ;

Chénard, S ;

Tremblay, M ;

Labrie, P .

TETRAHEDRON, 2001, 57 (15) :2965-2972

[7] Regioselective, diastereoselective, and enantioselective lithiation-substitution sequences: Reaction pathways and synthetic applications [J].

Beak, P ;

Basu, A ;

Gallagher, DJ ;

Park, YS ;

Thayumanavan, S .

ACCOUNTS OF CHEMICAL RESEARCH, 1996, 29 (11) :552-560

[8] Dearomatising cyclisation of lithiated l-naphthamides with a phenylglycinol-derived chiral auxiliary: asymmetric synthesis of an arylkainoid and a kainoid-like pyroglutamate [J].

Bragg, RA ;

Clayden, J ;

Bladon, M ;

Ichihara, O .

TETRAHEDRON LETTERS, 2001, 42 (20) :3411-3414

[9] Stereospecific formation of tetrasubstituted centres from trisubstituted centres during dearomatising anionic cyclisations [J].

Bragg, RA ;

Clayden, J .

TETRAHEDRON LETTERS, 1999, 40 (48) :8323-8326

[10] Diastereoselective ortholithiation and conformational control in stereospecific dearomatising anionic cyclisations [J].

Bragg, RA ;

Clayden, J .

TETRAHEDRON LETTERS, 1999, 40 (48) :8327-8331

← 1 2 3 →