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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 40, 2010 - Issue 11
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Original Articles

Combination of Novozym 435–Catalyzed Hydrolysis and Mitsunobu Reaction for Production of (R)-γ-Lactones

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Pages 1607-1613 | Received 09 Apr 2009, Published online: 06 May 2010
 

Abstract

Chiral γ-lactones of both enantiomers were synthesized with more than 90% optical purities. The key step was Novozym 435–catalyzed hydrolysis of racemic N-benzyl-4-acetoxyalkylamides. Additionally, because (R)-γ-lactones are predominant in apricot, mango, peach, passion fruit, and strawberry, synthesis was attempted using only one enantiomer selectively. The (R)-enantimer was synthesized with more than 80% total yield and more than 90% optical purity by a combination of Novozym 435–catalyzed hydrolysis and the Mitsunobu reaction.

ACKNOWLEDGMENTS

We are grateful to Novozymes A/S for the generous gift of Novozym 435. Financial support from Meiji University (Grant-in-Aid for Young Scientists of Meiji University) is gratefully acknowledged.

Notes

a Substrate: 1.0 mmol, MeOH: 3.0 mmol, Novozym 435: 0.4 g, Pr2O: 20 ml, 60 °C.

b Determined by GC using Chirasil-Dex CB column.

c E =ln[1 − c (1 + eep)]/ln[1 − c (1 − eep)], where c = ees/(ees + eep), ees = enantiomeric excess of (R)-1, eep = enantiomeric excess of (S)-1.

a Substrate: 1.0 mmol, MeOH: 3.0 mmol, Novozym 435: 0.4 g, i Pr2O: 20 ml, 60 °C.

b Nucleophile: 1.0 mmol, PPh3: 1.0 mmol, DIAD: 1.0 mmol, solvent: 5 ml, rt.

c Total yield based on rac-2.

d Determined by GC using Chirasil-Dex CB column.

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