Journal
ACS CATALYSIS
Volume 12, Issue 15, Pages 9655-9663Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acscatal.2c01671
Keywords
perfluoroarene interaction; chiral phosphoric acid; difluoroenoxysilane; Michael addition; theoretical study
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Funding
- Joint Fund of Zhejiang Provincial Natural Science Foundation [LTZ21B020001]
- Leading Innovative and Entrepreneur Team Introduction Program of Zhejiang [2019R01005]
- Natural Science Foundation of Zhejiang Province [LQ20B020005]
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A catalytic and highly enantioselective Mukaiyama-Michael addition of difluoroenoxysilanes to azadienes has been developed using perfluorinated aryl-incorporating chiral monophosphoric acid (PF-CPA) as an effective catalyst. The presence of perfluoroaryl substituents not only enhances catalytic activity but also creates a confined chiral environment for highly enantioselective transformations.
A catalytic and highly enantioselective Mukaiyama-Michael addition of difluoroenoxysilanes to azadienes has been developed using perfluorinated aryl-incorporating chiral monophosphoric acid (PF-CPA) as an effective, multipoint-controlled chiral catalyst. The inherent perfluoroaryl substituent is finely beneficial not only for achieving high catalytic activity but also for creating a compact and confined chiral environment for highly enantioselective transformations. Theoretical studies showed that the pi-pi interaction and hydrogen bond between PF-CPA and substrates play a crucial role in determining the stereochemical outcomes in comparison with those of phenyl, binaphthyl, and partially fluorinated aryls.
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