C(1)-substituted menthol derivatives: Self-removing chiral auxiliaries for asymmetric conjugate additions to cycloalkenones

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Abstract

C(1)-substituted (-)-menthone derivatives 3 were prepared by the stereoselective addition of the alkenyllithium reagents 9 to menthone (8) and subsequent acid catalyzed hydrolysis of the dioxolane protecting groups. Conjugate addition of cuprate reagents to enones 3a,b followed by a methanol quench directly gave the β-alkylcycloalkanones 7 via retro-aldol reactions in 80-91% ee.

Original languageEnglish (US)
Pages (from-to)1073-1074
Number of pages2
JournalTetrahedron Letters
Volume40
Issue number6
DOIs
StatePublished - Feb 5 1999

All Science Journal Classification (ASJC) codes

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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