A Simple Procedure for the Synthesis of -Hydroxyallenamides via Homoallenylation of Aldehydes. Academic Article uri icon

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.

published proceedings

  • Adv Synth Catal

author list (cited authors)

  • Kim, B., Gutierrez, O., Kozlowski, M. C., & Walsh, P. J.

citation count

  • 6

complete list of authors

  • Kim, Byeong-Seon||Gutierrez, Osvaldo||Kozlowski, Marisa C||Walsh, Patrick J

publication date

  • January 2018

publisher