Enantioselective Synthesis of β-Blockers via Hydrolytic Kinetic Resolution of Terminal Oxiranes by Using Bimetallic Chiral {{2,2′-[Cyclohexane-1,2-diylbis(nitrilomethylidyne)]bis[phenolato]}(2−)}cobalt ([Co(salen)])-Type Complexes

✍ Scribed by Rahul B. Kawthekar; Geon-Joong Kim

• Publisher: John Wiley and Sons
• Year: 2008
• Tongue: German
• Weight: 349 KB
• Volume: 91
• Category: Article
• ISSN: 0018-019X
• DOI: 10.1002/hlca.200890037

✦ Synopsis

Abstract

The synthesis of chirally pure β‐blockers was successfully achieved via hydrolytic kinetic resolution of butyl (±)‐4‐(oxiran‐2‐ylmethoxy)benzeneacetate ((±)‐1) and (±)‐4‐(oxiran‐2‐ylmethoxy)benzeneacetonitrile ((±)‐2) in the presence of bimetallic chiral [Co(salen)]‐type complexes. The newly synthesized bimetallic chiral [Co(salen)]‐type complexes exhibited excellent enantioselectivities of up to >98% ee in good yields (Tables 1–3).