Immobilized organocatalyst for asymmetric Michael addition in batch/flow: Diastereoselective synthesis of diverse indoloquinolizidines in flow

Moreshwar gave an oral communication at the International Symposium on Green Chemistry (ISGC 2022), La Rochelle, France (16-20 May, 2022).

AUTHORS
Moreshwar CHAUDHARI / INSTITUT CATALÀ D’INVESTIGACIÓ QUÍMICA (ICIQ), SPAIN, 16, AVINGUDA DELS
PAÏSOS CATALANS, TARRAGONA
Miquel PERICÀS / INSTITUT CATALÀ D’INVESTIGACIÓ QUÍMICA (ICIQ), SPAIN, 16, AVINGUDA DELS
PAÏSOS CATALANS, TARRAGONA

ABSTRACT
Asymmetric organocatalysis emerged as a promising approach for variety of challenging transformations.
However, due to their expensive, non-recyclable, and unstable nature inspired us to develop its immobilized
version which can be reused multiple times. Interestingly, integration of asymmetric immobilized organocatalysts
with continuous flow reactor can provide a breakthrough in the chiral revolution with process intensification owing
to economic and technical advantages. To this context, we have synthesized immobilized Jørgensen-Hayashi
catalysts and employed them for continuous production of asymmetric Michael adduct (precursor for alkaloid).
The produced Michael adducts (aldehyde-ester) employed as a precursor for synthesis of valuable natural
products/drugs. To our delight, for the first time, construction of a highly functionalized Indoloquinolizidines was
realized via highly diastereoselective Pictet-Splengler cyclisation-lactamization sequence using continuous-flow.
Using this approach exclusively cis H1/H12b geometry was obtained via thermodynamic control. In this talk, I will
discuss the notable results of our approach.

BIBLIOGRAPHY
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