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 -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.

Asymmetric Synthesis of 1-(2-Pyrrolyl)alkylamines by the Addition of Organometallic Reagents to Chiral 2-Pyrroleimines

GUALANDI, ANDREA;SAVOIA, DIEGO
2007

Abstract

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 -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.
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
G. Alvaro; R. Di Fabio; A. Gualandi; D. Savoia
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Utilizza questo identificativo per citare o creare un link a questo documento: http://hdl.handle.net/11585/59119
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