Journal
BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY
Volume 9, Issue -, Pages 1853-1857Publisher
BEILSTEIN-INSTITUT
DOI: 10.3762/bjoc.9.216
Keywords
allylic alkylation; asymmetric catalysis; fluorine; fluoro-beta-keto esters; Morita-Baylis-Hillman carbonates; natural product
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Funding
- NSFC [21072044, 21202034]
- Program for New Century Excellent Talents in University of the Ministry of Education [NCET-11-0938]
- Excellent Youth Foundation of Henan Scientific Committee [114100510003]
- Nanyang Technological University
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In the presence of a commercially available Cinchona alkaloid as catalyst, the asymmetric allylic alkylation of Morita-Baylis-Hillman carbonates, with alpha-fluoro-beta-keto esters as nucleophiles, have been successfully developed. A series of important fluorinated adducts, with chiral quaternary carbon centres containing a fluorine atom, was achieved in good yields (up to 93%), with good to excellent enantioselectivities (up to 96% ee) and moderate diastereoselectivities (up to 4:1 dr).
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