ASYMMETRIC INTRAMOLECULAR DIELS-ALDER REACTIONS OF SULFOXIMINE-ACTIVATED TRIENES

D CRAIG, N J GEACH, C J PEARSON, A M Z SLAWIN, A J P WHITE, D J WILLIAMS

Research output: Contribution to journalArticlepeer-review

28 Citations (Scopus)

Abstract

A series of N-substituted sulfoximidoyl-1,6,8-nonatrienes and 1,7,9-decatrienes were synthesised and subjected to thermal intramolecular Diels-Alder (IMDA) reactions to give diastereomeric mixtures of substituted bicyclo[4.3.0]nonanes and -[4.4.0]decanes. The reactions showed varying selectivities. Endo/exo selectivity was interpreted in terms of a combination of steric factors and the asynchronous nature of the cycloadditions. Diastereofacial selectivity could be rationalised by considering attack by the diene on the less hindered face of the conformationally extended vinylic sulfoximine dienophile.

Original languageEnglish
Pages (from-to)6071-6098
Number of pages28
JournalTetrahedron
Volume51
Issue number21
Publication statusPublished - 22 May 1995

Keywords

  • NUCLEOPHILIC EPOXIDATION
  • ABSOLUTE-CONFIGURATION
  • STEREOCHEMICAL ASPECTS
  • ALPHA
  • ALDEHYDES
  • METHYL

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