Tetrahedron

Studying competitive lithiations at alpha-, ortho-, and benzylic positions in various N-protected aniline derivatives

…, B Waldner, M Schnürch, MD Mihovilovic, P Stanetty

文献索引：Schmid, Martin; Waldner, Birgit; Schnuerch, Michael; Mihovilovic, Marko D.; Stanetty, Peter Tetrahedron, 2011 , vol. 67, # 16 p. 2895 - 2904

全文：HTML全文

被引用次数: 11

摘要

The directing effects of the t-BuOCONH–(NHBoc) and the t-BuCONH–(NH–pivaloyl) groups have been investigated on a series of differently substituted anilines. Depending on the nature of the directing group and the substrate, lithiation either occurred in the ortho-, benzylic-, or alpha-position. In general, it was observed that ortho-lithiation is the least facile process and alpha-lithiation slightly favored compared to lithiation in the benzylic position. ...