The Journal of Organic Chemistry

Highly Enantioselective Ring Opening of Cyclic Meso-Anhydrides to Isopropyl Hemiesters with Ti-TADDOLates: An Alternative to Hydrolytic Enzymes?

G Jaeschke, D Seebach

Index: Jaeschke, Georg; Seebach, Dieter Journal of Organic Chemistry, 1998 , vol. 63, # 4 p. 1190 - 1197

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Citation Number: 67

Abstract

The Lewis acid mediated transfer of an alkoxide ligand from the chiral ligand sphere of Ti- TADDOLate (1) to cyclic meso anhydrides to afford the corresponding hemiesters is described. By using this method a variety of structurally different anhydrides can be converted to isopropyl hemiesters with high enantioselectivities (enantiomer ratios up to 99: 1). We have also investigated Lewis acidic titanium complexes, which differ from 1 in the ...