Dynamic Kinetic Resolution of Homoallylic Alcohols: Application to the Synthesis of Enantiomerically Pure 5,6‐Dihydropyran‐2‐ones and δ‐Lactones |
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Authors: | Dr. Madeleine C. Warner Grigory A. Shevchenko Suzan Jouda Dr. Krisztián Bogár Prof. Jan‐E. Bäckvall |
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Affiliation: | Department of Organic Chemistry, Arrhenius Laboratory, Stockholm University, 106 91 Stockholm (Sweden) |
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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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Keywords: | dynamic kinetic resolution homoallylic alcohols lactones racemization ruthenium catalysis |
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