Asymmetric synthesis of 1-(2-pyrrolyl)alkylamines by the addition of organometallic reagents to chiral 2-pyrroleimines

Article abstract of DOI:10.1002/ejoc.200700597

The addition of organometallic (lithium, magnesium, zinc) reagents to 2-pyrroleimines derived from (S)-valinol and (S)-phenylglycinol gave N-substituted-1-(2-pyrrolyl)alkylamines with high yields and diastereoselectivities. The (S,S)-diastereomers were useful intermediates for the preparation of enantiopure 1-[1-(2-pyrrolyl)alkyl]aziridines by routine cyclization of the β-amino alcohol moiety and for the preparation of (S)-N-benzoyl 1-[1-(2-pyrrolyl)alkyl]amines and their N-substituted derivatives by oxidative cleavage of the chiral auxiliary. Wiley-VCH Verlag GmbH & Co. KGaA, 2007.