Determination of Configuration and Conformation of Isoxazolidines by Nuclear Overhauser Effect Difference Spectroscopy

Philip DeShong, C. Michael Dicken, Ronald R. Staib, Alan J. Freyer, Steven M. Weinreb

Research output: Contribution to journalArticle

95 Scopus citations

Abstract

The configurations of isoxazolidines 2, 3, 5, 7, and 10–12 have been assigned by analysis of NMR coupling constants and by nuclear Overhauser effect difference spectroscopy (NOEDS). The preferred solution conformations of isoxazolidines 3 and 5 were determined to be as in 3A/5A. It is proposed that these conformations are adopted to take advantage of the anomeric effect and to alleviate the unfavorable stereoelectronic lone pair-lone pair interaction in the N-O portion of the molecule (gauche effect).

Original languageEnglish (US)
Pages (from-to)4397-4403
Number of pages7
JournalJournal of Organic Chemistry
Volume47
Issue number23
DOIs
StatePublished - Jan 1 1982

All Science Journal Classification (ASJC) codes

  • Organic Chemistry

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