Diastereo- and enantioselective conjugate addition of α-keto esters to nitroalkenes: Complete switch in the enantioselectivity by tuning the metal center or rigidity of the ligand

doi:10.1016/S1872-2067(14)60199-6

Abstract

Abstract:

A series of efficient catalytic systems has been developed to control the dual enantioselectivity of the conjugate addition of α-keto esters to nitroalkenes. The use of the chiral diamine (1S,1'S)-1,1'-biisoindoline as a chiral ligand with either (Cu(OAc)₂·H₂O or Ni(OAc)₂·4H₂O as the catalyst provide facile access to the respective enantiomers resulting from the conjugate addition reaction with high levels of enantioselectivity (94% ee vs 93% ee). Furthermore, the use of Cu(OAc)₂·H₂O as the metal center allowed the enantioselectivity of the conjugate addition reaction to be switched through the tuning of the rigidity of the chiral diamine ligand (94% ee vs 94% ee).

Key words: Chiral diamine, Conjugate addition, Dual enantioselectivity, Metal center, Rigid ligand

Xiangning Chen, Han Zhou, Hanmin Huang. Diastereo- and enantioselective conjugate addition of α-keto esters to nitroalkenes: Complete switch in the enantioselectivity by tuning the metal center or rigidity of the ligand[J]. Chinese Journal of Catalysis, 2015, 36(1): 57-67.

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URL: https://www.cjcatal.com/EN/10.1016/S1872-2067(14)60199-6

https://www.cjcatal.com/EN/Y2015/V36/I1/57

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