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

• 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

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.