2,3-Dihydroisoindolones by cyclisation and rearomatisation of lithiated benzamides

被引:45
作者
Clayden, J [1 ]
Menet, CJ [1 ]
机构
[1] Univ Manchester, Dept Chem, Manchester M13 9PL, Lancs, England
关键词
D O I
10.1016/S0040-4039(03)00545-8
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Lithiation of tertiary aromatic N-benzyl amides generates [alpha]-amido benzyllithiums which cyclise with dearomatisation to cyclic extended enolates. Rearomatisation by oxidation, or, in the case of methoxy-substituted enolates, elimination, yields 2,3-dihydroisoindoles. Enantiomerically enriched products may be formed either by using a chiral base to lithiate the starting material or by using a chiral starting material. (C) 2003 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:3059 / 3062
页数:4
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