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Enantioselective Imine Reduction of Dihydro-β-carbolines by Fe-Thiosquaramide Catalyst
Manda Sathish1, Fabiane M Nachtigall2, Leonardo S Santos3
1Centro de Investigación de Estudios Avanzados del Maule, Vicerrectoría de Investigación y Postgrado, Universidad Católica del Maule, Talca 3605, Chile.
Abstract:
Enantioselective imine reduction of dihydro-β-carbolines (DHBCs) is a reliable and powerful tool to construct bioactive chiral tetrahydro-β-carbolines (THBCs). Here, we report an efficient enantioselective imine reduction employing in situ generated Fe-thiosquaramides (Fe-TSQs) 3a and 3b as asymmetric organometallic catalysts to produce chiral THBCs (2a-h). The catalyst 3a at 15 mol % was found to be suitable for the substrates with alkyl and aryl groups which afford corresponding chiral THBCs with excellent enantioselectivities (up to ee 99%).
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