Catalytic enantioselective aza Diels-Alder reactions of imino dienophiles

  • Yao S
  • Johannsen M
  • Hazell R
 et al. 
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1 mol% of catalyst is sufficient: The hetero Diels-Alder reaction of alpha-imino esters 1 with activated conjugated dienes 2 (R=H, Me) needs only 1 mol% of a 2,2prime-bis(diarylphosphanyl)-1,1prime-binaphthyl (BINAP) copper(I) complex as the catalyst to generate the adducts 3 in good yields and with enantioselectivities up to 96%. The reaction can also be carried out on gram scale! Tos=H3CC6H4SO2; TMS=Me3Si.

Author-supplied keywords

  • Asymmetric catalysis
  • Copper
  • Cycloadditions
  • Lewis acids
  • Synthetic methods

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