RT Journal Article T1 Multicomponent and multicatalytic asymmetric synthesis of furo[2,3- b ]pyrrole derivatives: further insights into the mode of action of chiral phosphoric acid catalysts A1 Cala, Lara A1 Villar Cruces, Pedro A1 Rodríguez de Lera, Ángel A1 Fañanás, Francisco J. A1 Álvarez Rodríguez, Maria Rosana A1 Rodríguez, Félix K1 3303.01 Tecnología de la Catálisis K1 2306 Química Orgánica K1 3303.05 Síntesis Química AB Multicomponent and multicatalytic reactions are those processes that try to imitate the way the enzymatic machinery transforms simple building blocks into complex products. The development of asymmetric versions of these reactions is a step forward in our dream of mirroring the exquisite selectivity of biological processes. In this context, the present work describes a new reaction for the asymmetric synthesis of furo[2,3-b]pyrrole derivatives from simple 3-butynamines, glyoxylic acid and anilines in the presence of a dual catalytic system, formed from a gold complex and a chiral phosphoric acid. Computations, aimed to understand the exceptional performance of 9-anthracenyl-substituted BINOLderived phosphoric acid catalyst, suggest a fundamental role of non-covalent interactions being established between the catalyst and the reagents for the outcome of the multicomponent process. Thelinear geometry of the anthracenyl substituent along with the presence of an electron-withdrawing group in the aniline and an aromatic substituent in the 3-butynamine derivative seem to be key structural factors to explain the experimental results and, particularly, the high stereoselectivity. PB Chemical Science SN 20416520 YR 2020 FD 2020 LK http://hdl.handle.net/11093/2279 UL http://hdl.handle.net/11093/2279 LA eng NO Chemical Science, 11(34): 9181-9190 (2020) NO Ministerio de Ciencia e Innovación | Ref. CTQ2016-76794-P DS Investigo RD 12-dic-2024