A New Synthesis of Highly Functional Nitrones through a Nitrosoketene Intermediate and Their Use for the Stereoselective Synthesis of Amino Acids

Nobuya Katagiri, Hiroshi Sato, Ayumu Kurimoto, Makoto Okada, Akemi Yamada, Chikara Kaneko

Research output: Contribution to journalArticlepeer-review

41 Citations (Scopus)

Abstract

Reaction of 5-isonitroso-2,2-dimethyl-1,3-dioxane-4,6-dione with various ketones under reflux in toluene gives 3-oxazolin-5-one 3-oxides (cyclic nitrones) via a nitrosoketene intermediate generated from the isonitroso derivative. The cyclic nitrones can be used for the stereoselective [3 + 2] dipolar cycloaddition to electron-rich olefins under high pressure to produce fused isoxazolidines. These isoxazolidines, in turn, are versatile intermediates for the stereoselective preparation of substituted α-amino acids.

Original languageEnglish
Pages (from-to)8101-8106
Number of pages6
JournalJournal of Organic Chemistry
Volume59
Issue number26
DOIs
Publication statusPublished - 1994 Dec 1

ASJC Scopus subject areas

  • Organic Chemistry

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