2026-04-17T16:58:49Zhttps://recercat.cat/oai/request

oai:recercat.cat:2072/5275492024-12-20T22:59:48Zcom_2072_300912com_2072_4427col_2072_301309

2022-11-03T13:00:57Z urn:hdl:2072/527549 An enantio- and diastereoselective approach to indoloquinolizidines in continuous flow Chaudhari, Moreshwar B. Gupta, Prachi Llanes, Patricia Zhou, Leijie Zanda, Nicola Pericàs, Miquel À. Merging polymer-supported asymmetric organocatalysis with continuous flow in a packed bed reactor has been used as the key, enantiodetermining step in a short synthesis of indoloquinolizidines. Using this approach, a highly enantioselective, solvent-free and rapid conjugate addition of dimethyl malonate to a diverse family of cinnamaldehydes in continuous flow, allowing the preparation of relevant oxodiesters in multigram amounts has been developed. The obtained Michael adducts have been used to complete an expedient diastereoselective synthesis of indoloquinolizidine via cascade Pictet–Splengler cyclisation-lactamisation in continuous flow. The conversion of enantiopure Michael adducts into δ-lactones via telescoped reduction/cyclisation in continuous flow has also been explored. 2022-11-03T13:00:57Z 2024-04-23T11:00:00Z 2022-11-03T13:00:57Z 2024-04-23T11:00:00Z 2022-08-10 2022-10-04 info:eu-repo/semantics/article info:eu-repo/semantics/publishedVersion http://hdl.handle.net/2072/527549 https://doi.org/10.1039/D2OB01462A eng Org. Biomol. Chem info:eu-repo/semantics/openAccess Org. Biomol.Chem. RECERCAT (Dipòsit de la Recerca de Catalunya)