Liebigs Annalen

Syntheses of β??Lactones, 6. One??Step Synthesis of β??Lactones by Aldolization of Ketones or Aldehydes with 1??Acylbenzotriazoles

C Wedler, K Kleiner, A Kunath, H Schick

Index: Wedler, Christine; Kleiner, Katharina; Kunath, Annamarie; Schick, Hans Liebigs Annales, 1996 , # 6 p. 881 - 885

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Citation Number: 13

Abstract

Abstract Benzotriazolides 1 of alkanoic acids with one hydrogen atom in α-position to the carboxamide group can be deprotonated with lithium diisopropylamide or lithium hexamethyldisilazanide to amide enolates 2 which condense at− 90 to− 95 C with ketones or aldehydes 3 to afford benzotriazolides of O-lithiated β-hydroxylalkanoic acids 4. These reactive carboxamide derivatives cyclize with elimination of lithium benzotriazolide to the ...