Synthesis of a new organocatalyst for Michael reactions

A new, easily tunable organocatalyst has been synthesized and applied in the Michael reaction of cyclohexanones to nitrostyrenes.

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(2S)-N-tert-Butoxycarbonyl-2-[(1′R)-1′,2′-dihydroxy-ethyl]-pyrrolidineC11H21NO4Ee, de >95% (NMR)[α]D20=-42.7 (c 1.1, CHCl3)Source of chirality: natural product, AD-mixβAbsolute configuration; (2S,1′R)

(2S)-N-tert-Butoxycarbonyl-2-[(1′R)-1′,2′-dibenzyloxy-ethyl]-pyrrolidineC25H33NO4Ee, de >95% (NMR)[α]D20=-70.1 (c 0.7, CHCl3)Source of chirality: natural product, AD-mixβAbsolute configuration; (2S,1′R)

(2S)-2-[(1′R)-1′,2′-Dibenzyloxy-ethyl]-pyrrolidineC20H25NO2Ee, de >95% (NMR)[α]D20=-34.6 (c 0.6, CHCl3)Source of chirality: natural product, AD-mixβAbsolute configuration; (2S,1′R)