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- W2952205436 abstract "Enantioselective formal hetero-Diels-Alder reactions of trifluoromethylated enones and 2-amino-1,3-butadienes generated in situ from aliphatic acyclic enones and chiral primary amines are reported. The corresponding tetrahydropyran-4-ones are formed in up to 94 % yield and with up to 94 % ee. The reaction was carried out through a stepwise mechanism, including initial aminocatalytic aldol condensation of 2-amino-1,3-butadiene to the trifluoromethylated carbonyl group followed by an intramolecular oxa-Michael addition. Both NMR investigation and theoretical calculations on the transition state indicate that the protonated tertiary amine could effectively activate the carbonyl group of the trifluoromethyl ketone to promote the addition process through hydrogen-bonding interaction of N-H⋅⋅⋅F and N-H⋅⋅⋅O simultaneously, and thus provide a chiral environment for the approach of amino-1,3-butadienes to the activated trifluoromethyl ketone, resulting in high enantioselectivity." @default.
- W2952205436 created "2019-06-27" @default.
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- W2952205436 date "2016-01-02" @default.
- W2952205436 modified "2023-09-28" @default.
- W2952205436 title "ChemInform Abstract: Enantio- and Diastereoselective Formal Hetero-Diels-Alder Reactions of Trifluoromethylated Enones Catalyzed by Chiral Primary Amines." @default.
- W2952205436 cites W2134481496 @default.
- W2952205436 doi "https://doi.org/10.1002/chin.201602127" @default.
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