Organocatalytic Asymmetric Michael–Acyl Transfer Reaction of α‐Nitroketones with 2‐Hydroxybenzylidene Ketones

Abstract

An organocatalytic asymmetric cascade Michael–acyl transfer reaction between 2‐hydroxybenzylidene ketones and α‐nitroketones is developed. The 9‐amino(9‐deoxy)‐epi‐hydroquinine catalyst in combination with benzoic acid was found to be the most effective for this reaction and the desired products were isolated in moderate to good yields and excellent enantioselectivities.

Organocatalytic asymmetric Michael/acyl transfer reaction between α-nitroketones and 4-arylidenepyrrolidine-2,3-diones

“…Consequently, our group developed an organocatalytic asymmetric Michael-acyl transfer reaction of α-nitroketones with unsaturated pyrazolones, 2-hydroxycinnamaldehydes, γ/δ-hydroxyenones, o-quinone methides, etc. [14][15][16][17][18]. Other groups also contributed contemporarily [19][20][21].…”

Organocatalytic Asymmetric Michael/Acyl Transfer Reaction between α-Nitroketones and 4-Arylidene- pyrrolidine-2,3-diones

“…In 2011, three research groups namely Wang, Yan and Kwong independently revealed organocatalytic asymmetric conjugate addition of αnitroketones to β,γ-unsaturated α-keto esters with concomitant acyl transfer reaction to the keto group [11][12][13]. Consequently, our group developed organocatalytic asymmetric Michael-acyl transfer reaction of α-nitroketones with unsaturated pyrazolones, 2-hydroxycinnamaldehydes, γ/δ-hydroxyenones, otrho-quinone methides etc [14][15][16][17][18]. Other groups also contributed contemporarily [19][20][21].…”