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...
Published in: | Chemistry – A European Journal |
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Main Authors: | , , , , |
Format: | Article in Journal/Newspaper |
Language: | English |
Published: |
Wiley
2013
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Subjects: | |
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 |
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 carboncarbon double bond afforded the corresponding δ‐lactones without loss of chiral information. |
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