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Application of a one-pot lipase resolution strategy for the synthesis of chiral γ- and δ-lactones

✍ Scribed by Ahmed Kamal; Mahendra Sandbhor; Ahmad Ali Shaik

Publisher
Elsevier Science
Year
2003
Tongue
English
Weight
185 KB
Volume
14
Category
Article
ISSN
0957-4166

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✦ Synopsis

A successful one-pot reduction of g-ketoesters, d-ketoesters and lactones to the corresponding 1,4-and 1,5-diols followed by a lipase catalyzed kinetic resolution coupled with hydrolysis to afford optically active diols is described. The synthetic utility of this one-pot method was illustrated by the oxidation of these chiral diols to respective chiral g-butyrolactone and d-lactones. Lipase from Pseudomonas cepacia, immobilized on ceramic afforded the product with high enantiomeric excess in good yields under mild reaction conditions. This approach has been used to develop a convenient enantioselective route for several gand d-lactones using achiral and corresponding racemic starting material.

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Lipase catalysed resolution of (R)- and
Lipase catalysed resolution of (R)- and (S)-1-trimethylsilyl-1-alkyn-3-ols: useful intermediates for the synthesis of optically active γ-lactones
✍ Pietro Allevi; Pierangela Ciuffreda; Mario Anastasia 📂 Article 📅 1997 🏛 Elsevier Science 🌐 English ⚖ 426 KB

Various (R)-and (S)-l-trimethylsilyl-l-alkyn-3-ols, chiral building units useful for the synthesis of biologically active compounds, have been efficiently resolved by enantioselective acetylation mediated by immobilized lipase PS. The resolution is applied to the synthesis of (R)-and (S)-5-octyl-2-(