A Simple Procedure for the Synthesis of ß-Hydroxyallenamides via Homoallenylation of Aldehydes.

A simple one-pot synthesis of ß-hydroxyallenamides is reported. This procedure entails chemo- and regioselective hydroboration of 3-en-1-ynyl-sulfonylamides with Cy2BH followed by homoallenylation of aldehydes to yield ß-hydroxyallenamides (up to 94% yield and >20:1 dr). Controlled synthesis of up to three continuous stereochemical elements was realized. Density functional theory (DFT) calculations suggest a concerted Zimmerman-Traxler chair-like transition state. Initial results suggest that enantio- and diastereoselective synthesis of ß-hydroxyallenamides with optically active hydroboration reagents is viable.