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

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) 2 BH) 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).