Nucleophilic substitution gone awry: A novel cyclopropanation reaction with a surprising stereochemical outcome

Charles J. Torborg, John J. Rabasco, Steven R. Kass

Research output: Contribution to journalArticlepeer-review

2 Scopus citations

Abstract

Lithium triethylborohydride reacts with the triisopropylbenzene sulfonate ester of 2-methoxy-5,5-dimethyl-2-vinyl-3-cyclohexen-1-ol (1) to afford 8-methoxy-6,6-dimethylspiro[2.5]oct-4-ene (3). Labeling studies reveal that this novel cyclopropane forming reaction proceeds with retention of configuration at the newly formed quaternary center.

Original languageEnglish (US)
Pages (from-to)6025-6028
Number of pages4
JournalTetrahedron Letters
Volume36
Issue number34
DOIs
StatePublished - Aug 21 1995

Keywords

  • cyclopropane formation
  • nucleophilic substitution
  • rearrangement
  • stereochemistry

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