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dc.contributor.author
Karak, Milandip  
dc.contributor.author
Barbosa, Luiz C. A.  
dc.contributor.author
Acosta, Jaime A. M.  
dc.contributor.author
Sarotti, Ariel Marcelo  
dc.contributor.author
Boukouvalas, John  
dc.date.available
2020-03-25T18:30:53Z  
dc.date.issued
2016-05  
dc.identifier.citation
Karak, Milandip; Barbosa, Luiz C. A.; Acosta, Jaime A. M.; Sarotti, Ariel Marcelo; Boukouvalas, John; Thermodynamically driven: Syn -selective vinylogous aldol reaction of tetronamides; Royal Society of Chemistry; Organic & Biomolecular Chemistry; 14; 21; 5-2016; 4897-4907  
dc.identifier.issn
1477-0520  
dc.identifier.uri
http://hdl.handle.net/11336/100748  
dc.description.abstract
A stereoselective vinylogous aldol reaction of N-monosubstituted tetronamides with aldehydes is described. The procedure is simple and scalable, works well with both aromatic and aliphatic aldehydes, and affords mainly the corresponding syn-aldol adducts. In many cases, the latter are obtained essentially free of their anti-isomers (dr > 99:1) in high yields (70-90%). Experimental and computational studies suggest that the observed diastereoselectivity arises through anti-syn isomer interconversion, enabled by an iterative retro-aldol/aldol reaction.  
dc.format
application/pdf  
dc.language.iso
eng  
dc.publisher
Royal Society of Chemistry  
dc.rights
info:eu-repo/semantics/openAccess  
dc.rights.uri
https://creativecommons.org/licenses/by-nc-sa/2.5/ar/  
dc.subject
TETRONAMIDES  
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VINILOGOUS ALDOL REACTION  
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TERMODYNAMICALLY CONTROLED  
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STEREOSELECTIVE SYNTHESIS  
dc.subject.classification
Química Orgánica  
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Ciencias Químicas  
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CIENCIAS NATURALES Y EXACTAS  
dc.title
Thermodynamically driven: Syn -selective vinylogous aldol reaction of tetronamides  
dc.type
info:eu-repo/semantics/article  
dc.type
info:ar-repo/semantics/artículo  
dc.type
info:eu-repo/semantics/publishedVersion  
dc.date.updated
2020-03-25T13:27:27Z  
dc.journal.volume
14  
dc.journal.number
21  
dc.journal.pagination
4897-4907  
dc.journal.pais
Reino Unido  
dc.journal.ciudad
Cambridge  
dc.description.fil
Fil: Karak, Milandip. Universidade Federal de Viçosa; Brasil. Universidade Federal de Minas Gerais; Brasil  
dc.description.fil
Fil: Barbosa, Luiz C. A.. Universidade Federal de Minas Gerais; Brasil. Universidade Federal de Viçosa; Brasil  
dc.description.fil
Fil: Acosta, Jaime A. M.. Universidade Federal de Minas Gerais; Brasil  
dc.description.fil
Fil: Sarotti, Ariel Marcelo. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Rosario. Instituto de Química Rosario. Universidad Nacional de Rosario. Facultad de Ciencias Bioquímicas y Farmacéuticas. Instituto de Química Rosario; Argentina  
dc.description.fil
Fil: Boukouvalas, John. Laval University; Canadá  
dc.journal.title
Organic & Biomolecular Chemistry  
dc.relation.alternativeid
info:eu-repo/semantics/altIdentifier/url/https://pubs.rsc.org/en/content/articlelanding/2016/OB/c6ob00895j#!divAbstract  
dc.relation.alternativeid
info:eu-repo/semantics/altIdentifier/doi/https://doi.org/10.1039/C6OB00895J  

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