1-Allyl-2-pyrroleimines obtained from (S)-valinol and (S)-phenylglycinol underwent highly diastereoselective addition of allylmagnesium chloride, used in excess amounts, to give the corresponding secondary amines with concomitant allyl to (Z)-1-propenyl isomerisation of the 1-pyrrole substituent. Transformation of the 2-aminoalcohol moiety to an oxazolidinone, or its cleavage and subsequent N-protection, followed by ring closing metathesis of the two alkene groups gave the unsaturated bicyclic compound. Full hydrogenation of the alkene function and the aromatic rings afforded the indolizidine derivative as a mixture of two or three diastereomers with a ratio which was dependent on the nature of both the N-substituent and the catalyst. The two prevalent diastereomers were isolated and their configuration was determined by X-ray crystallographic analysis.

Asymmetric synthesis of 8-aminoindolizidine from chiral 2-pyrroleimines

ALBANO, VINCENZO GIULIO;GUALANDI, ANDREA;MONARI, MAGDA;SAVOIA, DIEGO
2008

Abstract

1-Allyl-2-pyrroleimines obtained from (S)-valinol and (S)-phenylglycinol underwent highly diastereoselective addition of allylmagnesium chloride, used in excess amounts, to give the corresponding secondary amines with concomitant allyl to (Z)-1-propenyl isomerisation of the 1-pyrrole substituent. Transformation of the 2-aminoalcohol moiety to an oxazolidinone, or its cleavage and subsequent N-protection, followed by ring closing metathesis of the two alkene groups gave the unsaturated bicyclic compound. Full hydrogenation of the alkene function and the aromatic rings afforded the indolizidine derivative as a mixture of two or three diastereomers with a ratio which was dependent on the nature of both the N-substituent and the catalyst. The two prevalent diastereomers were isolated and their configuration was determined by X-ray crystallographic analysis.
V. G. Albano; A. Gualandi; M. Monari; D. Savoia
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Utilizza questo identificativo per citare o creare un link a questo documento: http://hdl.handle.net/11585/65477
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