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The Magnesium(II)‐Catalyzed Asymmetric Ketone–Ene Reaction under Solvent‐Free Conditions: Stereocontrolled Access to Enantioenriched Trifluoromethyl‐Substituted Compounds
Author(s) -
Zheng Ke,
Yang Yang,
Zhao Jiannan,
Yin Chengkai,
Lin Lili,
Liu Xiaohua,
Feng Xiaoming
Publication year - 2010
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201001412
Subject(s) - trifluoromethyl , catalysis , ketone , chemistry , substrate (aquarium) , yield (engineering) , ene reaction , solvent , magnesium , salt (chemistry) , organic chemistry , medicinal chemistry , materials science , alkyl , oceanography , metallurgy , geology
Salt of the (alkaline) earth : A highly efficient asymmetric ketone–ene reaction of trifluoropyruvate catalyzed by a chiral Mg(OTf) 2 – N,N′ ‐dioxide complex is described (see scheme). The catalyst system exhibits a broad substrate scope and the trifluoromethylated α‐hydroxy esters were obtained under solvent‐free conditions. The CC bond of the products offers a handle for further transformations and trifluoromethyl‐substituted spirocyclic compounds were synthesized in excellent ee and high yield.