Journal
CHEMISTRY-A EUROPEAN JOURNAL
Volume 17, Issue 29, Pages 8066-8070Publisher
WILEY-BLACKWELL
DOI: 10.1002/chem.201100929
Keywords
alcohols; asymmetric catalysis; FBSM; Morita-Baylis-Hillman reactions; organocatalysis
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Funding
- NSFC [21072044]
- Henan Province International Cooperation Foundation [104300510062]
- KAUST [4000000076]
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Enanatiopure beta-methyl-gamma-monofluoromethyl alcohols were prepared from the allylic alkylation between fluorobis(phenylsulfonyl) methane with Morita-Baylis-Hillman carbonates. The reaction was catalyzed by using the Cinchona alkaloid derivative, (DHQD)(2)AQN. The origin of the stereoselectivity was verified by DFT methods. Calculated geometries and relative energies of various transition states strongly support the observed stereoselectivity.
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