Diastereoselective synthesis of hydantoin- and isoxazoline-substituted dispirocyclobutanoids

Kyung Ho Park, Mark J. Kurth

Research output: Contribution to journalArticle

30 Scopus citations

Abstract

Synthetic strategies for constructing novel achiral cyclobutanoid isoxazolidinoimidazolidinedione heterocycles, with a generalized structure of II, have been developed via 1,3-dipolar cycloaddition and carbanilide cyclization transformations from methylenecyclobutane 13. The exo methylene cyclobutane system has made the realization of some diasteroselectivity possible, such that the H-bond (Boc-NH) directed product (i.e., 14) was obtained with 3:1 selectivity relative to the non-H-bond directed product (i.e., 15).

Original languageEnglish (US)
Pages (from-to)3520-3524
Number of pages5
JournalJournal of Organic Chemistry
Volume65
Issue number11
DOIs
StatePublished - Jun 2 2000

ASJC Scopus subject areas

  • Organic Chemistry

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