Dynamic Kinetic Resolution of Homoallylic Alcohols: Application to the Synthesis of Enantiomerically Pure 5,6‐Dihydropyran‐2‐ones and δ‐Lactones

Abstract Dynamic kinetic resolution of various homoallylic alcohols with the use of Candida antarctica lipase B and ruthenium catalyst 2 afforded homoallylic acetates in high yields and with high enantioselectivity. These enantiopure acetates were further transformed into homoallylic acrylates after...

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Bibliographic Details
Published in:Chemistry – A European Journal
Main Authors: Warner, Madeleine C., Shevchenko, Grigory A., Jouda, Suzan, Bogár, Krisztián, Bäckvall, Jan‐E.
Format: Article in Journal/Newspaper
Language:English
Published: Wiley 2013
Subjects:
Antarc*
Antarctica
Online Access:http://dx.doi.org/10.1002/chem.201301980
https://api.wiley.com/onlinelibrary/tdm/v1/articles/10.1002%2Fchem.201301980
http://onlinelibrary.wiley.com/wol1/doi/10.1002/chem.201301980/fullpdf
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Summary:Abstract Dynamic kinetic resolution of various homoallylic alcohols with the use of Candida antarctica lipase B and ruthenium catalyst 2 afforded homoallylic acetates in high yields and with high enantioselectivity. These enantiopure acetates were further transformed into homoallylic acrylates after hydrolysis of the ester function and subsequent DMAP‐catalyzed esterification with acryloyl chloride. After ring‐closing metathesis 5,6‐dihydropyran‐2‐ones were obtained in good yields. Selective hydrogenation of the carboncarbon double bond afforded the corresponding δ‐lactones without loss of chiral information.

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