✦ LIBER ✦
Enzymes in Organic Synthesis, 26. Synthesis of Enantiomerically Enriched 2,3- and 3,4-Dimethylpentan-5-olides by Lipase-Catalyzed Regio- and Enantioselective Alcoholysis of cis- and trans-2,3-Dimethylpentanedioic Anhydrides
✍ Scribed by Ozegowski, Rüdiger ;Kunath, Annamarie ;Schick, Hans
- Publisher
- John Wiley and Sons
- Year
- 2006
- Tongue
- English
- Weight
- 680 KB
- Volume
- 1996
- Category
- Article
- ISSN
- 0947-3440
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✦ Synopsis
Abstract
The enzyme‐catalyzed regio‐ and enantioselective alcoholysis of racemic cis‐ and trans‐2,3‐dimethylpentanedioc anhydride in the presence of Novozym 435 from Candida antarctica afforded two of the eight possible monoesters with an enantiomeric excess higher than 90%. Regioselective reductions of these monoesters with lithium borohydride or borane/dimethyl sulfide furnished four enantiomerically highly enriched dimethylpentan‐5‐olides, which are versatile chiral intermediates.