期刊
CHEMISTRY-A EUROPEAN JOURNAL
卷 21, 期 33, 页码 11773-11778出版社
WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.201501897
关键词
enantioselectivity; enones; hydrogen bonds; organocatalysis; oxygen heterocycles
资金
- NSFC [21102116, 21203153]
- Innovative Research Team in College of Sichuan Province [14TD0016]
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 NHF and NHO simultaneously, and thus provide a chiral environment for the approach of amino-1,3-butadienes to the activated trifluoromethyl ketone, resulting in high enantioselectivity.
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