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

研究成果: Article査読

42 被引用数 (Scopus)

抄録

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.

本文言語English
ページ(範囲)8101-8106
ページ数6
ジャーナルJournal of Organic Chemistry
59
26
DOI
出版ステータスPublished - 1994 12 1

ASJC Scopus subject areas

  • 有機化学

フィンガープリント

「A New Synthesis of Highly Functional Nitrones through a Nitrosoketene Intermediate and Their Use for the Stereoselective Synthesis of Amino Acids」の研究トピックを掘り下げます。これらがまとまってユニークなフィンガープリントを構成します。

引用スタイル