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
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 reducti...
| Published in: | Liebigs Annalen |
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| Main Authors: | , , |
| Format: | Article in Journal/Newspaper |
| Language: | English |
| Published: |
Wiley
1996
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| Subjects: | |
| Online Access: | http://dx.doi.org/10.1002/jlac.199619960916 https://api.wiley.com/onlinelibrary/tdm/v1/articles/10.1002%2Fjlac.199619960916 https://onlinelibrary.wiley.com/doi/full/10.1002/jlac.199619960916 |
| Summary: | 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. |
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