Synthesis and transformations of enantiomeric 1,2-disubstituted monoterpene derivatives

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48 Citations (Scopus)

Abstract

Regio- and stereospecific addition of chlorosulfonyl isocyanate to (+)- and (-)-α-pinene 1 resulted in enantiomerically pure β-lactams 2, which were converted to enantiomeric β-amino esters 3 and 1,3-amino alcohols 4 and 6 with ee >99%. The resulting 1,3-difunctional compounds 3, 4 and 6 were transformed to fused saturated 1,3-heterocycles such as tetrahydro-1,3-oxazines 7 and 9, 2,4-pyrimidinedione 11 and 2-thioxopyrimidin-4-one 13 enantiomers.

Original languageEnglish
Pages (from-to)4571-4579
Number of pages9
JournalTetrahedron Asymmetry
Volume11
Issue number22
DOIs
Publication statusPublished - Nov 17 2000

ASJC Scopus subject areas

  • Catalysis
  • Physical and Theoretical Chemistry
  • Organic Chemistry
  • Inorganic Chemistry

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