These tools will no longer be maintained as of December 31, 2024. Archived website can be found here. PubMed4Hh GitHub repository can be found here. Contact NLM Customer Service if you have questions.


Pubmed for Handhelds

PUBMED FOR HANDHELDS

Search MEDLINE/PubMed

  • Title: Organocatalytic Asymmetric Synthesis of Dihydrobenzoxazinones Bearing Trifluoromethylated Quaternary Stereocenters.
    Author: Lou H, Wang Y, Jin E, Lin X.
    Journal: J Org Chem; 2016 Mar 04; 81(5):2019-26. PubMed ID: 26882280.
    Abstract:
    Chiral phosphoric acid-catalyzed enantioselective aza-Friedel-Crafts reaction of trifluoromethyl benzoxazinones with pyrroles is reported. Under mild conditions, a range of enantioenriched dihydrobenzoxazinones bearing trifluoromethylated quaternary stereocenters could be obtained in good to excellent yield and ee. A remarkable fluorine effect is observed, and preliminary mechanistic studies combined with theory calculations suggest that triple-hydrogen-bonding interactions hold the transition structure rigidly and allow the bulky substituents of the catalyst to influence the enantioselectivity.
    [Abstract] [Full Text] [Related] [New Search]