Journal
CHEMISTRY-A EUROPEAN JOURNAL
Volume 23, Issue 3, Pages 519-523Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.201604920
Keywords
aldol; enone; isocoumarin; organocatalysis; trifluoromethyl
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Funding
- South University of Science and Technology of China [FRG-SUSTC1501A-57]
- National Natural Science Foundation of China [NSFC 21302089]
- Special Funds for the Development of Strategic Emerging Industries in Shenzhen [JCYJ20160429191918729]
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A new method has been developed for the organocatalytic enantioselective benzylation and aldol-hemiacetalization of alpha,beta-unsaturated trifluoromethyl ketones with toluene derivatives in the presence of a tertiary amine-thiourea catalyst. This method represents a facile and efficient strategy for the asymmetric synthesis of optically active 3,4-dihydroisocoumarins bearing a trifluoromethylated tetrasubstituted carbon stereocenter with high enantioselectivity. Notably, this strategy was used to synthesize several chiral trifluoromethylated analogues of typharin with high efficiency.
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