Stereoselective syntheses and transformations of chiral 1,3-aminoalcohols and 1,3-diols derived from nopinone

Zsolt Szakonyi, Tímea Gonda, Sándor Balázs Ötvös, Ferenc Fülöp

Research output: Contribution to journalArticle

20 Citations (Scopus)

Abstract

A library of 1,3-difunctionalized pinane derivatives were synthesized and applied as chiral catalysts in the addition of diethylzinc to benzaldehyde. 1,3-Aminoalcohol 6a was prepared from (-)-nopinone 2 via stereoselective Mannich condensation and reduction of the resulting β-amino ketone 4. The key aminoalcohol 6a was transformed into primary, secondary and tertiary substituted aminoalcohols in order to study the effect of the substituent on catalytic activity. Starting from (-)-nopinone, cis- and trans-β-hydroxy esters 15 and 16 were prepared in a two-step stereoselective synthesis. Reduction of the hydroxy esters resulted in pinane-based 1,3-diols, while hydrolysis of the esters, followed by DCC-mediated amidation and subsequent reduction, led to cis- and trans-N-benzyl-1,3-aminoalcohols 8 and 23. trans-N-Benzyl-1,3-aminoalcohol 8 was also prepared by selective mono-debenzylation of 6a via a continuous-flow process in an H-Cube® system. The resulting aminoalcohols and diols were applied as chiral catalysts in the reaction of diethylzinc and benzaldehyde.

Original languageEnglish
Pages (from-to)1138-1145
Number of pages8
JournalTetrahedron Asymmetry
Volume25
Issue number15
DOIs
Publication statusPublished - Aug 15 2014

ASJC Scopus subject areas

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

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