title: Thermodynamically driven, syn-selective vinylogous aldol reaction of tetronamides.
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.
authors.affiliation: Department of Chemistry, Instituto de Ciências Exatas, Universidade Federal de Minas Gerais, Av. Pres. Antônio Carlos, 6627, Campus Pampulha, Belo Horizonte, 31270-901, MG, Brazil. lcab@ufmg.br.
authors.forename: Milandip
authors.initials: M
authors.lastname: Karak
authors.forename: Luiz C A
authors.initials: LC
authors.lastname: Barbosa
authors.forename: Jaime A M
authors.initials: JA
authors.lastname: Acosta
authors.forename: Ariel M
authors.initials: AM
authors.lastname: Sarotti
authors.forename: John
authors.initials: J
authors.lastname: Boukouvalas