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

WF Bailey, MR Luderer, MJ Mealy

Index: Bailey, William F.; Luderer, Matthew R.; Mealy, Michael J. Tetrahedron Letters, 2003 , vol. 44, # 28 p. 5303 - 5305

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Citation Number: 20

Abstract

The ether-soluble dilithio species (2), derived from N-allyl-2-bromoaniline (1) upon treatment with t-BuLi at− 78° C, cyclizes when warmed to+ 5° C in the presence of TMEDA to give a (1- 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.