ChemInform Abstract: Organocatalytic Asymmetric Aza‐Michael Additions

Abstract

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Lipase‐catalyzed aza‐Michael addition of amines to acrylates in supercritical carbon dioxide

“…[1][2][3][4][5][6] Therefore, many methods have been well established for aza-Michael addition to produce -amino carbonyl compounds. [7][8][9] In general, this reaction can be catalyzed by acid, base, or metal catalysts. 10,11 However, the competition of aminolysis is a major drawback in aza-Michael additions when amines are used as nucleophiles, and the low chemoselectivity of aza-Michael additions limit its utility in organic synthesis.…”

Highly enantioselective Michael addition of α‐nitroacetate to α,β‐unsaturated pyrazolamide catalyzed by a bifunctional squaramide

“…(entries [6][7][8][9]. High levels of enantioselectivities maintained in all solvents evaluated, however, toluene allowed access to the desired adduct 3aa with slightly higher isolated yield (entries 4 vs entries [6][7][8][9].…”

“…Therefore, the development of asymmetric version of this reaction has constituted an actively pursued field, and significant progress has been achieved. [1][2][3][4] Among all documented nucleophiles, [5][6][7] α-nitroacetate [8][9][10][11] is generally utilized as masked amino acid in various organic transformations. 12,13 Moreover, α-nitroacetate also provides profound derivation after the initial reaction, such as decarboxylation [14][15][16] and denitration.…”