[Complete 1,3-Asymmetric Induction into 3-Methyl-4-(3-Acetylpyrrol-1- yl)Butanal to 1-Acetyl-6-Methyl-8-Hydroxy-5,6,7,8-Tetrahydroindolizine Cyclization ]

Giuliano      Alagona; Raffaello      Lazzaroni; Silvia      Rocchiccioli; Roberta      Settambolo

Letters in Organic Chemistry

Author(s): Giuliano Alagona, Raffaello Lazzaroni, Silvia Rocchiccioli and Roberta Settambolo

DOI: 10.2174/157017806774964486

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[Complete 1,3-Asymmetric Induction into 3-Methyl-4-(3-Acetylpyrrol-1- yl)Butanal to 1-Acetyl-6-Methyl-8-Hydroxy-5,6,7,8-Tetrahydroindolizine Cyclization ]

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Abstract

The formation of 1-acetyl-6-methyl-8-hydroxy-5,6,7,8-tetrahydroindolizine (3) from 3-methyl-4-(3- acetylpyrrol-1-yl)butanal (2), coming from the rhodium catalyzed hydroformylation of 2-methyl-3-(3- acetylpyrrol-1-yl)prop-1-ene (1), is reported. Evidences for both the complete diastereoselective cyclization of 2 and the configuration determination in 3 via 1H, 13 C and IR spectra are reported.

Keywords: pyrrolylbutanal, rhodium-catalyst, hydroxytetrahydroindolizines, hydroformylation, 1, 3-asymmetric induction

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