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Regioselective and diastereoselective borono-mannich reactions with pinacol allenylboronate

Journal Article


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Abstract


  • The first documented study of the borono-Mannich (Petasis) reactions of pinacol allenylboronate is described. The reactions of salicylaldehyde and primary and secondary amines are highly regioselective and give homopropargylamine and α-allenylamine products, respectively. In contrast, glycoaldehyde and chiral α-hydroxyaldehydes give exclusively anti-β-amino-β-allenyl alcohol products, irrespective of the nature of the amine component. These reactions are highly regio- and diastereoselective and can be employed using an enantiomerically enriched α-hydroxyaldehyde without detectable racemization.

UOW Authors


Publication Date


  • 2015

Citation


  • Thaima, T. & Pyne, S. G. (2015). Regioselective and diastereoselective borono-mannich reactions with pinacol allenylboronate. Organic Letters, 17 (4), 778-781.

Scopus Eid


  • 2-s2.0-84923361707

Ro Full-text Url


  • http://ro.uow.edu.au/cgi/viewcontent.cgi?article=3744&context=smhpapers

Ro Metadata Url


  • http://ro.uow.edu.au/smhpapers/2723

Has Global Citation Frequency


Number Of Pages


  • 3

Start Page


  • 778

End Page


  • 781

Volume


  • 17

Issue


  • 4

Place Of Publication


  • United States

Abstract


  • The first documented study of the borono-Mannich (Petasis) reactions of pinacol allenylboronate is described. The reactions of salicylaldehyde and primary and secondary amines are highly regioselective and give homopropargylamine and α-allenylamine products, respectively. In contrast, glycoaldehyde and chiral α-hydroxyaldehydes give exclusively anti-β-amino-β-allenyl alcohol products, irrespective of the nature of the amine component. These reactions are highly regio- and diastereoselective and can be employed using an enantiomerically enriched α-hydroxyaldehyde without detectable racemization.

UOW Authors


Publication Date


  • 2015

Citation


  • Thaima, T. & Pyne, S. G. (2015). Regioselective and diastereoselective borono-mannich reactions with pinacol allenylboronate. Organic Letters, 17 (4), 778-781.

Scopus Eid


  • 2-s2.0-84923361707

Ro Full-text Url


  • http://ro.uow.edu.au/cgi/viewcontent.cgi?article=3744&context=smhpapers

Ro Metadata Url


  • http://ro.uow.edu.au/smhpapers/2723

Has Global Citation Frequency


Number Of Pages


  • 3

Start Page


  • 778

End Page


  • 781

Volume


  • 17

Issue


  • 4

Place Of Publication


  • United States