Direct access to tetrasubstituted cyclopentenyl scaffolds through a diastereoselective isocyanide-based multicomponent reaction
作者:Vitor A. Fernandes、Rafaely N. Lima、Yoisel B. Broterson、Meire Y. Kawamura、Radell Echemendía、Alexander F. de la Torre、Marco A. B. Ferreira、Daniel G. Rivera、Marcio W. Paixão
DOI:10.1039/d1sc04158d
日期:——
of multicomponentreactions is described to produce structurally unique, tetrasubstituted cyclopentenyl frameworks. An asymmetric Michael addition–hemiacetalization between α-cyanoketones and α,β-unsaturated aliphatic aldehydes was performed for constructing cyclic hemiacetals, which were next employed as chiral bifunctional substrates in a new diastereoselective intramolecular isocyanide-based multicomponent
描述了一种将有机催化的立体控制与多组分反应的多样性生成特征相结合的有效策略,以产生结构独特的四取代环戊烯基框架。在α-氰酮和α,β-不饱和脂肪醛之间进行不对称迈克尔加成-半缩醛化,以构建环状半缩醛,随后将其用作新型非对映选择性分子内异氰化物多组分反应中的手性双功能底物。这种方法提供了多种结构复杂的化合物,包括高立体选择性(高达 >99% ee 和高达 >99 : 1 dr)和中等到高产率的肽模拟物和天然产物混合物。