Diisopinocampheylborane-Mediated Reductive Aldol Reactions: Highly Enantio- and Diastereoselective Synthesis of syn Aldols from N-Acryloylmorpholine


  • We thank the National Institutes of Health (GM038436) for support of this research. We also sincerely thank Prof. Glenn Micalizio and Dr. Daniel Canterbury for fruitful discussions and comments on this work.


original image

Cutting costs, cutting corners: In an inexpensive and straightforward synthesis of syn-propionamide aldols, formation of the Z enolborinate by the hydroboration of 4-acryloylmorpholine with diisopinocampheylborane ((Ipc)2BH) was followed by aldol reactions with achiral and chiral aldehydes to provide syn-α-methyl-β-hydroxymorpholinecarboxamides with excellent enantio- and diastereoselectivity (see scheme; R=alkyl, alkenyl, aryl, heteroaryl).