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

ABSTRACT: A simple one-pot synthesis of β-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 β-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 β-hydroxyallenamides with optically active hydroboration reagents is viable.

SUBMITTER: Kim BS 

PROVIDER: S-EPMC5977997 | biostudies-literature | 2018 Apr

REPOSITORIES: biostudies-literature