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

Abstract

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).