A Chiral N-Tetrafluoroiodobenzyl-N-sulfonyl Aminomethylpyrrolidine Catalyst for the Enantioselective Michael/Hemiaminal Formation Cascade Reaction of α,β-Unsaturated Iminoindoles with Aldehydes

Abstract A chiral N-2,3,4,5-tetrafluoro-6-iodobenzyl-N-sulfonyl ­aminomethylpyrrolidine tetrafluoroacetic acid salt was designed as an ­iodinated enamine organocatalyst for the enantioselective ­Michael/hemiaminal formation cascade reaction of α,β-unsaturated ­iminoindoles with aldehydes. The use of this iodinated enamine ­catalyst furnished anti-α-carbolinol derivatives in high yields and high stereoselectivities.