A Simple Procedure for the Synthesis of -Hydroxyallenamides via Homoallenylation of Aldehydes.
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abstract
A simple one-pot synthesis of -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 -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 -hydroxyallenamides with optically active hydroboration reagents is viable.