Regio- and stereoselective synthesis of the enantiomers of monoterpene-based β-amino acid derivatives

Z. Szakonyi, T. Martinek, Reijo Sillanpää, F. Fülöp

Research output: Contribution to journalArticle

15 Citations (Scopus)

Abstract

The regio- and stereospecific addition of chlorosulfonyl isocyanate to cis-δ-pinene enantiomers has furnished monoterpene-fused β-lactams. The observed regioselectivity can be explained by ab initio DFT modeling of transition state structures. In contrast with the less reactive α-pinane-fused β-lactam 4, the resulting β-lactams 5 and 13 containing an amino group connected to a secondary carbon possess similar reactivity to the cycloalkane-fused analogues and can be easily converted to the β-amino acid and its protected derivatives. The base-catalyzed isomerization of the cis-amino ester afforded the corresponding trans-amino ester in moderate yield.

Original languageEnglish
Pages (from-to)2442-2447
Number of pages6
JournalTetrahedron Asymmetry
Volume18
Issue number20
DOIs
Publication statusPublished - Oct 10 2007

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Monoterpenes
Lactams
Enantiomers
enantiomers
amino acids
Amino acids
esters
Derivatives
Amino Acids
isocyanates
Esters
synthesis
Cycloparaffins
isomerization
Regioselectivity
reactivity
analogs
Isomerization
Discrete Fourier transforms
carbon

ASJC Scopus subject areas

  • Inorganic Chemistry
  • Organic Chemistry
  • Materials Chemistry
  • Drug Discovery

Cite this

Regio- and stereoselective synthesis of the enantiomers of monoterpene-based β-amino acid derivatives. / Szakonyi, Z.; Martinek, T.; Sillanpää, Reijo; Fülöp, F.

In: Tetrahedron Asymmetry, Vol. 18, No. 20, 10.10.2007, p. 2442-2447.

Research output: Contribution to journalArticle

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