Synthesis of bornene-2,2'-diamino-1,1'-binaphthalene conjugates in palladium-catalysed aminocarbonylations

Gábor Mikle, Borbála Boros, L. Kollár

Research output: Contribution to journalArticle

5 Citations (Scopus)

Abstract

Palladium-catalysed aminocarbonylation of a terpenoic iodoalkene (2-iodo-bornene) model compound with both enantiomerically pure and racemic 2,2'-diamino-1,1'-binaphthalene (BINAM) as the N-nucleophile was carried out. All of the diastereoisomers of the monocarboxamide (N-bornenyl carboxamide) and dicarboxamide (N,. N'-dinorbornenylcarboxamide) derivatives were synthesised. The diastereoselectivities of the aminocarbonylation were investigated in both cases: either racemic BINAM was used as the N-nucleophile in the aminocarbonylation of enantiomerically pure 2-iodobornene or racemic iodobornene was aminocarbonylated with enantiomerically pure BINAM with moderate diastereoselectivities. In this way, all possible diastereoisomers of binaphthalene-bornene conjugates were synthesised in moderate to high yields by asymmetric (diastereoselective) aminocarbonylation.

Original languageEnglish
JournalTetrahedron Asymmetry
DOIs
Publication statusAccepted/In press - Mar 1 2016

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Nucleophiles
nucleophiles
Palladium
palladium
synthesis
Derivatives
2,2'-diamino-1,1'-binaphthalene

ASJC Scopus subject areas

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

Cite this

Synthesis of bornene-2,2'-diamino-1,1'-binaphthalene conjugates in palladium-catalysed aminocarbonylations. / Mikle, Gábor; Boros, Borbála; Kollár, L.

In: Tetrahedron Asymmetry, 01.03.2016.

Research output: Contribution to journalArticle

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