Enantioselective Synthesis of Oxindole‐Derived α‐Aryl‐β‐Amino Acid Derivatives and δ‐Lactams with Homophthalic Anhydrides

Abstract

AbstractA highly diastereo‐ and enantioselective Mannich reaction of isatin‐derived N‐Boc imines with homophthalic anhydrides is disclosed for the first time, which allows the direct synthesis of a wide range of oxindole‐derived α‐aryl‐β‐amino acids with two adjacent carbon stereogenic centers in a highly stereoselective fashion (up to >95:5 dr & >99% ee). The resulted Mannich adducts can be easily converted to chiral spirocyclic δ‐lactams with retention of the stereoslectivities.magnified image