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%).