The Journal of Organic Chemistry

Ester homologation revisited: a reliable, higher yielding and better understood procedure

CJ Kowalski, RE Reddy

Index: Kowalski, Conrad J.; Reddy, Rajarathnam E. Journal of Organic Chemistry, 1992 , vol. 57, # 28 p. 7194 - 7208

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Citation Number: 62

Abstract

Enolate anions 3 and 6, prepared via enolization of a-bromo and dibromo ketones 4 and 6 were converted in high yield to ynolate anions 10 by respective addition of lithium tetramethylpiperidide (to effect deprotonation, 3-7) or butyllithium (to effect metal-halogen exchange, 6-7). Mixtures of such enolates were also obtainable from esters 1 on a large- scale (25 mol) via in situ formation and addition of lithiodibromomethane (from methylene ...