2026-04-17T12:10:32Zhttps://recercat.cat/oai/requestoai:recercat.cat:2072/5275492024-12-20T22:59:48Zcom_2072_300912com_2072_4427col_2072_301309
RECERCAT
author
Chaudhari, Moreshwar B.
author
Gupta, Prachi
author
Llanes, Patricia
author
Zhou, Leijie
author
Zanda, Nicola
author
Pericàs, Miquel À.
2022-11-03T13:00:57Z2024-04-23T11:00:00Z
2022-11-03T13:00:57Z2024-04-23T11:00:00Z
2022-10-04
http://hdl.handle.net/2072/527549
https://doi.org/10.1039/D2OB01462A
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.
eng
An enantio- and diastereoselective approach to indoloquinolizidines in continuous flow
info:eu-repo/semantics/article info:eu-repo/semantics/publishedVersion
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