4.4 Article

Mg/BOX complexes as efficient catalysts for the enantioselective Michael addition of malonates to β-trifluoromethyl-α,β-unsaturated ketones and their N-tosyl imines

Journal

TETRAHEDRON
Volume 80, Issue -, Pages -

Publisher

PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tet.2020.131897

Keywords

Enantioselective Michael addition; Mg/BOX catalyst; Malonates; beta-Trifluoromethyl-alpha,beta-Unsaturated ketones; N-tosyl imines

Funding

  1. Agencia Estatal de Investigacion (AEI-MINECO)
  2. FEDER [CTQ2017-84900-P]
  3. Generalitat Valenciana [AICO/2020/068]
  4. Generalitat Valenciana and FEDER-EU [APOST/2016/139]
  5. Spanish government [IJC2018-036682-I]

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Magnesium (II)-BOX complexes catalyze the enantioselective Michael addition of malonates to beta-trifluoromethyl enones and their N-sulfonyl imines to give ketones or (E)-enamines bearing a trifluoromethylated stereogenic center, respectively, with good yields and high enantiomeric excesses. The magnesium complexes exhibit higher activity and stereoselectivity than zinc and copper analogues in these reactions.
Magnesium (II)-BOX complexes catalyze the enantioselective Michael addition of malonates to beta-trifluoromethyl enones and their N-sulfonyl imines to give ketones or (E)-enamines bearing a trifluoromethylated stereogenic center, respectively, with good yields and high enantiomeric excesses. Magnesium complexes proved to be more active and stereoselective than zinc and copper analogues in these reactions. (C) 2020 Elsevier Ltd. All rights reserved.

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