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Variations in site of lithiation of N-[(2-(4-Methoxyphenyl)ethyl)]pivalamide; Use in ring substitution

Smith, Keith, El-Hiti, Gamal A. and Alshammari, Mohammed 2013. Variations in site of lithiation of N-[(2-(4-Methoxyphenyl)ethyl)]pivalamide; Use in ring substitution. Synlett 24 (1) , pp. 117-119. 10.1055/s-0032-1317859

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Abstract

Lithiation of N-[(2-(4-methoxyphenyl)ethyl)]pivalamide at -20 to 0 oC with three mole equivalents of n-BuLi in anhydrous THF, followed by reactions with various electrophiles, gives high yields of products involving ring substitution ortho- to the pivaloylaminoethyl group, which was unexpected in view of earlier results reported with t-BuLi.

Item Type: Article
Date Type: Publication
Status: Published
Schools: Chemistry
Subjects: Q Science > QD Chemistry
Uncontrolled Keywords: N-[2-(4-methoxyphenyl)ethyl]pivalamide; directed lithiation; synthesis; electrophile; dilithium intermediate
Publisher: Georg Thieme Verlag
ISSN: 0936-5214
Date of First Compliant Deposit: 30 March 2016
Last Modified: 04 Jun 2017 04:41
URI: http://orca-mwe.cf.ac.uk/id/eprint/42879

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