SHORTPAPER	Synthesis 2006: 1575-1577   DOI: 10.1055/s-2006-926461
© Georg Thieme Verlag Stuttgart · New York
Efficient Two-Step Synthesis of Salicylaldehydes via Directed ortho-Lithiation of in situ N-Silylated O-Aryl N-Isopropylcarbamates
Matthias Kauch, Dieter Hoppe*
Westfälische Wilhelms-Universität Münster, Organisch-Chemisches Institut, Corrensstraße 40, 48149 Münster, Germany Fax: +49(251)8336531; e-Mail: dhoppe@uni-muenster.de;
Received 23 December 2005

Abstract

O-Aryl N-isopropylcarbamates, conveniently prepared from phenols and isopropyl isocyanate, are subjected to an efficient ortho-lithiation protocol to afford the corresponding salicylaldehydes in a one-pot operation in high yields.

Key words

carbanions - formylation - lithiation - phenols - salicylaldehydes