Stereoselective synthesis and transformations of pinane-based 1,3-diaminoalcohols

T�mea Gonda, Attila Bal�zs, G�bor T�th, Ferenc F�l�p, Z. Szakonyi

Research output: Contribution to journalArticle

3 Citations (Scopus)

Abstract

A library of pinane-based 1,3-diaminoalcohols and 5-aminomethyloxazolidin-2-ones was developed from commercially available (1R)-(−)-myrtenol which was transformed to N-trichloroacetyl protected allyl amine via Overmann rearrangement followed by stereoselective epoxidation with mCPBA resulting in key intermedier epoxy-amine. In order to obtain the diaminoalcohol moiety, aminolysis and azidolysis of the oxirane ring was performed. The cleavage of the oxirane ring proceeded regioselectively, affording N-trichloroacetyl protected 1,3-diaminoalcohols and oxazolidin-2-ones, which were obtained also via a thermal cyclisation. Since N deprotection of diaminoalcohols was unsuccessful under varied conditions, the protecting group was changed and Boc-protected analogues were synthesised. In this case, removal of the Boc protecting group was successful resulting in the planned diamino alcohols. An unexpected extreme δ Meα-9 value (0.11�ppm) was measured for the dibenzylaminomethyl-substituted oxazolidine-2-one, and the stereostructure was refined by means of DFT geometry optimization. The obtained potential catalysts were applied in the test reaction of benzaldehyde and diethylzinc with low to moderate enantioselectivities (up to 74% ee).

Original languageEnglish
Pages (from-to)2638-2648
Number of pages11
JournalTetrahedron
Volume73
Issue number18
DOIs
Publication statusPublished - Jan 1 2017

Keywords

  • Catalyst
  • Diaminoalcohol
  • Monoterpene
  • Oxazolidinone
  • Stereochemistry

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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