title: Regioselective and diastereoselective borono-Mannich reactions with pinacol allenylboronate.
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.
authors: School of Chemistry, University of Wollongong , Wollongong, New South Wales 2522, Australia.
authors: Thanaphat
authors: T
authors: Thaima
authors: Stephen G
authors: SG
authors: Pyne