Tetrahedron: Asymmetry

Enzymatic desymmetrization of prochiral 2, 3-bis (acetoxymethyl) bicyclo [2.2. 1] hepta-2, 5-diene and 2, 3-bis (hydroxymethyl) bicyclo [2.2. 1] hepta-2, 5-diene

M Ranchoux, JM Brunel, G Iacazio, G Buono

Index: Ranchoux, Magali; Brunel, Jean-Michel; Iacazio, Gilles; Buono, Gerard Tetrahedron Asymmetry, 1998 , vol. 9, # 4 p. 581 - 587

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Citation Number: 14

Abstract

Enzymatic desymmetrization of the title compound 1 is reported using various commercially available lipases in hydrolysis and alcoholysis reactions or ester synthesis. In this area, lipase Amano AK (Pseudomonas sp.) proved to be the best lipase whatever the experimental conditions used. The monoacetate product 2 is indifferently obtained with more than 95% enantiomeric excess (ee) as the levorotatory enantiomer 2a or the ...