Synthesis and transformation of novel cyclic β-amino acid derivatives from (+)-3-carene

Szilvia Gyónfalvi, Zsolt Szakonyi, Ferenc Fülöp

Research output: Contribution to journalArticle

54 Citations (Scopus)

Abstract

The regio- and stereoselective addition of chlorosulfonyl isocyanate to (+)-3-carene 1 resulted in β-lactam 2, which was converted to N-Boc-β-amino acid 4, β-amino ester 7, and carboxamide derivatives 18 and 20 via N-Boc activation and mild ring opening. The corresponding β-amino ester 7 was transformed to 2-thioxopyrimidin-4-one 11 and 2,4-pyrimidinedione 13. LAH reduction of 5 and 7 resulted in amino alcohols 6 and 8. The reaction of 8 with phenyl isothiocyanate, followed by cyclisation, furnished 1,3-oxazine 15.

Original languageEnglish
Pages (from-to)3965-3972
Number of pages8
JournalTetrahedron Asymmetry
Volume14
Issue number24
DOIs
Publication statusPublished - Dec 12 2003

ASJC Scopus subject areas

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

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