3,3′‐Bimorpholine Derivatives as a New Class of Organocatalysts for Asymmetric Michael Addition.

Abstract

Aldehydes Q 0320 3,3'-Bimorpholine Derivatives as a New Class of Organocatalysts for Asymmetric Michael Addition. -A new efficient catalyst is developed for the reaction of a variety of aliphatic aldehydes with aromatic nitroolefins and a vinyl sulfone. Sterically hindered aldehydes are unreactive, even after 8 days. Otherwise good yields, good dia-and enantioselectivities are observed. Aliphatic nitroolefin (Vc) reacts stereoselectively but with low yield. -(MOSSE, S.; LAARS, M.; KRIIS, K.; KANGER, T.; ALEXAKIS*, A.; Org. Lett. 8 (2006) 12, 2559-2562; Dep. Org. Chem., Univ. Geneva, CH-1211 Geneva 4, Switz.; Eng.) -R. Steudel 43-083

Synthesis, crystal structure analysis, spectral investigations, DFT computations and molecular dynamics and docking study of 4-benzyl-5-oxomorpholine-3-carbamide, a potential bioactive agent

“…An investigation of the aromatic substitution on antihyperlipidemic morpholine derivatives with antioxidant activity is reported in literature [8]. In addition to pharmacological properties, morpholines are widely used in organic synthesis, however their uses is most frequently restricted to application as simple bases, N-alkylating agent, catalysts, and chiral auxiliaries [9][10][11][12][13][14][15]. Thus, up to now, numerous strategies toward the synthesis of substituted morpholines have been reported [16][17][18][19][20][21][22][23][24][25].…”

Asymmetric synthesis of (R)-baclofen and (3S,4S)-tetflupyrolimet via “on water” organocatalytic addition reactions: a tip on catalyst screening

“…Asymmetric Michael addition reactions generate key precursors for abundant natural products and pharmaceutical drugs. 1 Among the various Michael acceptors, nitroolefins 2 have garnered special interest due to their high reactivity and the facile transformation ability of the nitro group. 3 This area of research has yielded an elegant synthesis of a diverse range of valuable nitrogen-containing chiral molecules via γ-lactam intermediates (Scheme 1a).…”

Design, synthesis and application of chiral tetraoxacalix[2]arene[2]triazine‐based organocatalysts in asymmetric Michael addition reactions

“…Since, these reactions led to the formation of optically active γ-nitro carbonyl compounds, 14,15 which are found to be important building blocks in organic/medicinal chemistry. 19,20 The common examples include chiral pyrrolidine-type diamines, 21,22 chiral guanidines, 23,24 L-proline derivatives, 25,26 chiral diamines, 27,28 Cinchona-based catalysts, 29,30 urea and thiourea-derived bifunctional organocatalysts. [16][17][18] Because of the increasing interest in this area, a wide range of highly efficient chiral organocatalysts have appeared in the literature for asymmetric Michael additions since Barbas and List independently reported the first organocatalytic studies using L-proline.…”

“…[16][17][18] Because of the increasing interest in this area, a wide range of highly efficient chiral organocatalysts have appeared in the literature for asymmetric Michael additions since Barbas and List independently reported the first organocatalytic studies using L-proline. 19,20 The common examples include chiral pyrrolidine-type diamines, 21,22 chiral guanidines, 23,24 L-proline derivatives, 25,26 chiral diamines, 27,28 Cinchona-based catalysts, 29,30 urea and thiourea-derived bifunctional organocatalysts. 31,32 In the last decade, we have made considerable efforts to the synthesis and application of calixarenes.…”