RIS ID
98857
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.
Grant Number
ARC/DP130101968
Publication Details
Thaima, T. & Pyne, S. G. (2015). Regioselective and diastereoselective borono-mannich reactions with pinacol allenylboronate. Organic Letters, 17 (4), 778-781.