Directed Lithiation of N′-[2-(4-Methoxyphenyl)ethyl]-N,N-dimethylurea and tert-Butyl [2-(4-Methoxyphenyl)ethyl]carbamate

Abstract

N′-[2-(4-Methoxyphenyl)ethyl]-N,N-dimethylurea and tert-butyl [2-(4-methoxyphenyl)ethyl]carbamate are doubly lithiated on the nitrogen and ortho to the directing metalating group at –20 to 0 °C with three mole equivalents of n-BuLi in anhydrous THF. Reactions of the dilithium reagents produced in situ with various electrophiles give high yields of the corresponding substituted products. In the case of the urea, side-products due to lithiation and substitution on one of the methyl groups of the urea unit are obtained in low yields (0–17%).

Key words

directed lithiation - side-chain lithiation - N′-[2-(4-methoxyphenyl)ethyl]-N,N-dimethylurea - tert-butyl [2-(4-methoxyphenyl)ethyl]carbamate - electrophile

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