1210360-60-3Relevant articles and documents
Self-assembled fibrillar networks of a multifaceted chiral squaramide: Supramolecular multistimuli-responsive alcogels
Schiller, Jana,Alegre-Requena, Juan V.,Marqués-López, Eugenia,Herrera, Raquel P.,Casanovas, Jordi,Alemán, Carlos,Díaz Díaz, David
, p. 4361 - 4374 (2016)
Chiral N,N′-disubstituted squaramide 1 has been found to undergo self-assembly in a variety of alcoholic solvents at low concentrations leading to the formation of novel nanostructured supramolecular alcogels. The gels responded to thermal, mechanical, op
Enantioselective Synthesis of Cyclohexenol Derivatives from ?-Aryl-Substituted Enals via an Organocatalyzed Three-Component Reaction
Majee, Debashis,Jakkampudi, Satish,Arman, Hadi D.,Zhao, John C.-G.
, p. 9166 - 9170 (2019/11/14)
A three-component reaction between ?-aryl-substituted α,β-unsaturated aldehydes and nitroalkenes was realized by using cinchona alkaloid-derived (thio)ureas and squaramides via the dienolate intermediates. This unprecedented 1,3- A nd 1,5-reactivity of dienolates of the ?-aryl-α,β-unsaturated aldehydes led to the formation of cyclohexenol derivatives with four contiguous stereogenic centers and a chiral substituent at C2 with good diastereoselectivities and high ee values. Such reactivities of the dienolates are totally different from those of the corresponding dienamine intermediates.
Total Syntheses of Pyroclavine, Festuclavine, Lysergol, and Isolysergol via a Catalytic Asymmetric Nitro-Michael Reaction
Bhunia, Subhajit,Chaudhuri, Saikat,Bisai, Alakesh
supporting information, p. 11234 - 11238 (2017/08/26)
A catalytic enantioselective construction of vicinal stereocenters is reported. The reaction takes advantage of thiourea-catalyzed intramolecular nitronate addition onto α,β-unsaturated ester to afford exceptional levels of enantioselectivity (up to 97 % ee) with moderate diastereoselectivity (up to 4:1). Using this method, a cross-conjugated ester was synthesized in few steps, from which a 6-endo-trig cyclisation led to the formation of all required functionalities for total syntheses of ergot alkaloids. The strategy not only offers first total syntheses of ergot alkaloids, festuclavine (1 c), and pyroclavine (1 e), and but also an efficient and general approach to other congeners such as, lysergol (1 b), and isolysergol (1 d).