Preparation of differentially 1,3-disubstituted indolines by intramolecular carbolithiation

被引：19

作者：

Bailey, WF

Luderer, MR

Mealy, MJ

机构：

[1] Univ Connecticut, Dept Chem, Storrs, CT 06269 USA

[2] H Lundbeck & Co AS, Proc Dev, DK-4500 Lumsaas, Denmark

来源：

TETRAHEDRON LETTERS | 2003年 / 44卷 / 28期

关键词：

D O I：

10.1016/S0040-4039(03)01204-8

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The ether-soluble dilithio species (2), derived from N-allyl-2-bromoaniline (1) upon treatment with t-BuLi at -78degreesC, cyclizes when warmed to +5degreesC in the presence of TMEDA to give a (l-lithio-3-indolinyl)methyllithium (3) that may be differentially functionalized by sequential addition of electrophiles. The cyclization of 2 to 3 proceeds enantioselectively when conducted in the presence of (1S,2S)-(+)-N,O-dimethylpseudoephedrine. (C) 2003 Elsevier Science Ltd. All rights reserved.

引用

页码：5303 / 5305

页数：3