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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, Email:

M. Kauch, D. Hoppe, Synthesis, 2006, 1575-1577.

DOI: 10.1055/s-2006-926461


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.

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Key Words

carbanions, formylation, lithiation, directed ortho metalation, phenols, salicylaldehydes

ID: J66-Y2006-1230