Base-promoted reactions of α-azido ketones with aldehydes and ketones: A novel entry to α-azido-β-hydroxy ketones and 2,5-dihydro-5-hydroxyoxazoles

T. Patonay, Robert V. Hoffman

Research output: Contribution to journalArticle

45 Citations (Scopus)

Abstract

The base-promoted reaction of α-azido ketones with aldehydes and ketones provides a new and simple route to either α-azido-β-hydroxy ketones, which are valuable 1,2,3-trifunctionalized synthons, or 2,5-dihydro-5-hydroxyoxazoles, which are a little known type of oxazoline. These two products are formed by the electrophilic trapping of two different anions that are produced sequentially during the reaction. The α-azido-β-hydroxy ketones are formed by an aldol reaction between an enolate of the α-azidoketone and an aldehyde. The 2,5-dihydro-5-hydroxyoxazoles are formed by electrophilic trapping of an imino anion which is produced by nitrogen loss from the α-azido ketone enolate.

Original languageEnglish
Pages (from-to)2368-2377
Number of pages10
JournalJournal of Organic Chemistry
Volume60
Issue number8
Publication statusPublished - 1995

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Ketones
Aldehydes
Anions
Nitrogen

ASJC Scopus subject areas

  • Organic Chemistry

Cite this

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abstract = "The base-promoted reaction of α-azido ketones with aldehydes and ketones provides a new and simple route to either α-azido-β-hydroxy ketones, which are valuable 1,2,3-trifunctionalized synthons, or 2,5-dihydro-5-hydroxyoxazoles, which are a little known type of oxazoline. These two products are formed by the electrophilic trapping of two different anions that are produced sequentially during the reaction. The α-azido-β-hydroxy ketones are formed by an aldol reaction between an enolate of the α-azidoketone and an aldehyde. The 2,5-dihydro-5-hydroxyoxazoles are formed by electrophilic trapping of an imino anion which is produced by nitrogen loss from the α-azido ketone enolate.",
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AU - Hoffman, Robert V.

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N2 - The base-promoted reaction of α-azido ketones with aldehydes and ketones provides a new and simple route to either α-azido-β-hydroxy ketones, which are valuable 1,2,3-trifunctionalized synthons, or 2,5-dihydro-5-hydroxyoxazoles, which are a little known type of oxazoline. These two products are formed by the electrophilic trapping of two different anions that are produced sequentially during the reaction. The α-azido-β-hydroxy ketones are formed by an aldol reaction between an enolate of the α-azidoketone and an aldehyde. The 2,5-dihydro-5-hydroxyoxazoles are formed by electrophilic trapping of an imino anion which is produced by nitrogen loss from the α-azido ketone enolate.

AB - The base-promoted reaction of α-azido ketones with aldehydes and ketones provides a new and simple route to either α-azido-β-hydroxy ketones, which are valuable 1,2,3-trifunctionalized synthons, or 2,5-dihydro-5-hydroxyoxazoles, which are a little known type of oxazoline. These two products are formed by the electrophilic trapping of two different anions that are produced sequentially during the reaction. The α-azido-β-hydroxy ketones are formed by an aldol reaction between an enolate of the α-azidoketone and an aldehyde. The 2,5-dihydro-5-hydroxyoxazoles are formed by electrophilic trapping of an imino anion which is produced by nitrogen loss from the α-azido ketone enolate.

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