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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 39, 2009 - Issue 9
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Original Articles

Synthesis of (S)-γ-Lactones with a Combination of Lipase-Catalyzed Resolution and Mitsunobu Reaction

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Pages 1570-1582 | Received 03 Aug 2008, Published online: 02 Apr 2009
 

Abstract

Six kinds of (S)-γ-lactones [e.g., (S)-γ-decalactone, (S)-γ-undecalactone, and (S)-γ-jasmolactone] were synthesized with 71–88% yields and >97% optical purities by combining lipase-catalyzed resolution with the Mitsunobu reaction.

ACKNOWLEDGMENT

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) is gratefully acknowledged.

Notes

a Yield based on rac-1c.

b Determined by GC using Chirasil-Dex CB column.

a Yield based on rac-1c.

b Determined by GC using Chirasil-Dex CB column.

a Yield based on rac-1.

b Determined by GC using Chirasil-Dex CB column.

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