Preparation of α, n-dilithiotoluene equivalents. Synthesis of tamoxifen

M Yus, DJ Ramón, I Gómez

Index: Yus, Miguel; Ramon, Diego J.; Gomez, Inmaculada Tetrahedron, 2003 , vol. 59, # 18 p. 3219 - 3225

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Citation Number: 20

Abstract

The successive reaction of chlorobenzyl alcohols with n-butyllithium and lithium powder in the presence of a substoichiometric amount of 4, 4′-di-tert-butylbiphenyl (DTBB) at− 78° C yields the expected (lithiooxymethyl) phenyllithium derivative, which is trapped by reaction with different ketones. The subsequent arene-catalysed lithiation at 25° C permits the one- pot chemoselective lithiation of the primary benzyl alcoholate in the presence of a tertiary ...