[3 + 2] Cycloadditions of carbonyl oxides to imines: An alternative approach to the synthesis of 1,2,4-dioxazolidines

Kevin J. McCullough, Mitsuyuki Mori, Toshihiko Tabuchi, Hideyuki Yamakoshi, Shigekazu Kusabayashi, Masatomo Nojima

Research output: Contribution to journalArticle

Abstract

Carbonyl oxides, derived from the ozonolysis of vinyl ethers, readily undergo [3 + 2] cycloadditions with imines, affording the corresponding 1,2,4-dioxazolidines 6a-z in the isolated yields of 14-97%. High degrees of stereoselectivity are observed in certain cases, suggesting that this [3 + 2] cycloaddition proceeds by a concerted process. In competition experiments, a relative order of reactivity towards carbonyl oxides was tentatively deduced: nitrone > imine > thioketone > carbonyl compound. The structure of the 1,2,4-dioxazolidine 6d was unambiguously determined by the X-ray crystallographic analysis. 1,2,4-Dioxazolidines were found to undergo ring cleavage reactions on either thermolysis or treatment with base.

Original languageEnglish
Pages (from-to)41-48
Number of pages8
JournalJournal of the Chemical Society, Perkin Transactions 1
Issue number1
Publication statusPublished - 1995

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