Regioselective transformation of 6/5-fused bicyclic isoxazolidines to second-generation cyclic aldonitrones

Basem Moosa, Shaikh A. Ali

Research output: Contribution to journalArticlepeer-review

4 Scopus citations

Abstract

The cycloaddition reactions of 4-(2-hydroxy-2-propyl)-3,4,5,6- tetrahydropyridine 1-oxide with mono- and di-substituted alkenes have been found to be highly stereo- as well as face-selective. In solution, the 6/5 fused bicyclic cycloadducts remain solely as the cis-fused invertomers in order to accommodate the bulky tertiary substituent 2-hydroxy-2-propyl in the equatorial orientation. The cycloadducts, upon peracid oxidation, leads to the exclusive formation of synthetically important second-generation cyclic aldonitrones. The stereo- and face-selectivity of the cycloaddition reactions of these second-generation nitrones bearing substituents at C(4) and C(6) have been briefly examined. One interesting finding was that treatment of the first generation nitrone i.e., 4-(2-hydroxy-2-propyl)-3,4,5,6-tetrahydropyridine 1-oxide, with mercury(II) oxide afforded a novel bicyclic nitrone, 1-oxa-5,6-dehydro-6-aza-bicyclo[3,2,1]heptane 6-oxide.

Original languageEnglish (US)
Pages (from-to)132-148
Number of pages17
JournalArkivoc
Volume2010
Issue number10
DOIs
StatePublished - Jul 29 2010

Keywords

  • Conformational analysis
  • Cyclic nitrones
  • Face selectivity
  • Nitrone cycloaddition
  • Peracid oxidation
  • Stereoselectivity

ASJC Scopus subject areas

  • Organic Chemistry

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