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Title: Chiral Bifunctional Thioureas and Squaramides and Their Copolymers as Recoverable Organocatalysts. Stereoselective Synthesis of 2-Substituted 4-Amino-3-nitrobenzopyrans and 3-Functionalized 3,4-Diamino-4H-Chromenes
Authors: Andrés García, José María
Maestro Fernández, Alicia
Valle, María
Pedrosa Sáez, Rafael
Issue Date: 2018
Publisher: American Chemical Society
Description: Producción Científica
Citation: Journal of Organic Chemistry, 2018, 83 (10), pp 5546–5557
Abstract: Novel styryl-substituted thioureas and squaramides were obtained in three steps from commercially available 4-hydroxy-3,5-dichloroaniline. These organocatalysts promote cascade reactions in high yields and excellent stereoselection. By using only a 5 mol % loading of catalyst, it is possible to obtain 2,3,4-trisubstituted benzopyrans by reaction of α-amido sulfones derived from salicyladehydes and nitrostyrenes or 2,3,4-trisubstituted 4H-chromenes by reaction of the same α-amido sulfones with (phenylsulfonyl)acetonitrile in excellent diastereo- and enantioselectivities. Two polymeric thioureas and squaramides were prepared by copolymerization of the best monomeric catalysts with styrene and divinylbenzene and used for the same transformations. These polymers behave also as excellent stereoselective catalysts that can be recovered and reused for five cycles.
Classification: Aminobenzopiranos
ISSN: 0022-3263
Peer Review: SI
Sponsor: Ministerio de Economía, Industria y Competitividad (Project FEDER-CTQ2014-59870-P)
Junta de Castilla y León (programa de apoyo a proyectos de investigación - Project FEDER-VA115P17)
Publisher Version:
Language: eng
Rights: info:eu-repo/semantics/openAccess
Appears in Collections:CINQUIMA - Artículos de revista
DEP67 - Artículos de revista

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