Journal
ACS CATALYSIS
Volume 7, Issue 7, Pages 4736-4740Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acscatal.7b01178
Keywords
dienamine; organocatalysis; fluorinated quaternary carbon; allylic fluoride; CH hydrogen bond
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Funding
- MEXT/JSPS KAKENHI [JP16H00778, JP16KT0165, JP17K05757, JP17K14451]
- Institute of Quantum Chemical Exploration
- Okinawa Intellectual Cluster Program
- Grants-in-Aid for Scientific Research [16H00778, 17K14451, 16KT0165, 17K05757] Funding Source: KAKEN
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Fluorination of dienamines generated by alpha-branched enals and 6'-hydroxy-9-amino-9-deoxy-epi-quinidine (30 mol %) with NSFI show excellent alpha-regioselectivity to construct allylic fluorides containing a highly stereocontrolled quaternary fluorinated carbon (E/Z >= 20/1 and up to 93% enantiometric excess (ee)). By DFT calculation, the quinuclidine moiety of the catalyst was shown to function as a coordinating group to promote a reaction at the proximal alpha-position, and the nonclassical CH hydrogen bond plays an important role in the high enantioselectivity.
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