New bifunctional 1,3-diamine organocatalysts derived from (+)-camphoric acid for asymmetric Michael addition of 1,3-dicarbonyl compounds to nitroolefins
Novel 1,3-diamine-derived bifunctional thiourea and squaramide organocatalysts were synthesized from (+)-camphoric acid. These catalysts were easily obtained in up to two to five synthetic steps, in a flexible approach that facilitates their structure variation. Their catalytic activity was examined in the asymmetric Michael addition of 1,3-dicarbonyl compounds to several trans-β-nitrostyrenes. Yields up to 98% and enantiomeric excesses up to 74% and high diastereoselectivities when applicable (dr up to 93:7) were obtained in these reactions showing that 1,3-diamine-derived bifunctional thioureas are efficient organocatalysts.
Murtinho, Dina,Rénio, Márcia,Ventura, M. Rita
(2022/02/19)
Novel chiral hydrogen bond donor catalysts based on a 4,5-diaminoxanthene scaffold: Application to enantioselective conjugate addition of 1,3-dicarbonyl compounds to nitroalkenes
Novel chiral hydrogen bond donor catalysts based on a 4,5-diamino-9, 9′-dimethylxanthene skeleton were designed and synthesized. Among the phenylurea-amide hybrid molecules prepared from various natural/unnatural chiral amino acids, the phenylalanine-deri
Ephedrine- and pseudoephedrine-derived thioureas in asymmetric michael additions of keto esters and diketones to nitroalkenes
Ephedrine-derived bifunctional thioureas have been synthesized and applied as organocatalysts in Michael additions of 1,3-dicarbonyl compounds to nitroalkenes. Georg Thieme Verlag Stuttgart.
Flock, Angelika Marie,Krebs, Anke,Bolm, Carsten
supporting information; experimental part
p. 1219 - 1222
(2010/08/20)
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