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)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).