Michael addition of dibenzylamine to (-)- and (+)-tert-butyl myrtenate, (-)-2 and (+)-2, derived from (-)- and (+)-myrtenal, furnished monoterpene-based β-amino acid derivatives in highly stereospecific reactions. The resultant amino esters (-)-3 and (+)-3 were transformed to unsubstituted, mono- and disubstituted and Fmoc-protected amino acids (-)-6-11 and (+)-6-11, which are promising building blocks for the synthesis of β-peptides and 1,3-heterocycles. The microwave-assisted conjugate addition of nitromethane to α,β-unsaturated esters (-)-12 and (+)-12 likewise resulted in nitro esters (-)-13 and (+)-13 in highly stereospecific reactions. Compounds (-)-13 and (+)-13 were successfully transformed into γ-amino acids (-)-16 and (+)-16 in two steps.
ASJC Scopus subject areas
- Physical and Theoretical Chemistry
- Organic Chemistry
- Inorganic Chemistry