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 ORCID: https://orcid.org/0000-0001-9687-8747 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:	03 May 2023 18:32
URI:	https://orca.cardiff.ac.uk/id/eprint/42879

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