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Keywords:

  • asymmetric allylic alkylation;
  • cyclohexenes;
  • dicyanoalkenes;
  • organocatalysis;
  • Morita–Baylis–Hillman carbonates

Abstract

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The first highly enantioselective allylic–allylic alkylation of α,α-dicyanoalkenes and Morita–Baylis–Hillman carbonates by dual catalysis of (DHQD)2AQN and (S)-BINOL has been investigated. Excellent stereoselectivities have been achieved for a broad spectrum of substrates (d.r. > 99:1, up to 99 % ee). The multifunctional allylic products could be efficiently converted to a range of complex chiral cyclic frameworks. EWG=electron-withdrawing group, (DHQD)2AQN=hydroquinidine (anthraquinone-1,4-diyl) diether, (S)-BINOL =(S)-(−)-1,1′-bi-2-naphthol.

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