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  • Synthesis of indolizidines from optically pure α-amino acids via stereocontrolled rhodium-catalyzed hydroformylation of N-allylpyrroles.

Synthesis of indolizidines from optically pure α-amino acids via stereocontrolled rhodium-catalyzed hydroformylation of N-allylpyrroles.

Chirality (2011-08-23)
Raffaello Lazzaroni, Roberta Settambolo
RESUMO

Indolizidine alkaloids have attracted considerable attention because of their vast array of structural diversity and varied biological activity. This article relates the results that we obtained in the field of the total synthesis of indolizidines from α-amino acids, based on the rhodium-catalyzed hydroformylation of N-allylpyrroles intermediates. The formed pyrrolylbutanals undergo an intramolecular cyclodehydration to 5,6-dihydroindolizines, which are fully hydrogenated to indolizidines. All reaction sequences are stereocontrolled: indeed, the chiral center in the starting amino acid is transferred into 5,6-dihydroindolizine moiety with complete stereochemical integrity and the new stereogenic center at C9 carbon atom in the final indolizidines is generated in only one configuration.

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Sigma-Aldrich
Rhodium, powder, 99.95% trace metals basis
Rhodium, foil, not light tested, 25x25mm, thickness 0.00025mm, permanent polyester support, 99.9%
Rhodium, foil, 25x25mm, thickness 0.1mm, as rolled, 99.9%
Rhodium, foil, not light tested, 25x25mm, thickness 0.0005mm, permanent polyester support, 99.85%
Rhodium, microfoil, disks, 10mm, thinness 0.1μm, specific density 124μg/cm2, permanent mylar 3.5μm support, 99.9%
Rhodium, foil, not light tested, 50x50mm, thickness 0.006mm, as rolled, 99.9%
Rhodium, foil, 12mm disks, thickness 0.5mm, as rolled, 99.9%
Rhodium, foil, not light tested, 25x25mm, thickness 0.012mm, as rolled, 99.9%
Rhodium, foil, not light tested, 25x25mm, thickness 0.00075mm, permanent polyester support, 99.85%
Rhodium, microfoil, disks, 25mm, thinness 0.25μm, specific density 310μg/cm2, permanent mylar 3.5μm support, 99.99%
Rhodium, microfoil, disks, 10mm, thinness 0.25μm, specific density 310μg/cm2, permanent mylar 3.5μm support, 99.99%
Rhodium, foil, light tested, 25x25mm, thickness 0.05mm, as rolled, 99.9%
Rhodium, foil, 25x25mm, thickness 0.15mm, as rolled, 99.9%
Rhodium, microfoil, disks, 10mm, thinness 0.50μm, specific density 620μg/cm2, permanent mylar 3.5μm support, 99.99%
Rhodium, foil, light tested, 25x25mm, thickness 0.05mm, as rolled, x-ray quality, 99.9%
Rhodium, foil, light tested, 15x15mm, thickness 0.05mm, as rolled, 99.9%
Rhodium, foil, not light tested, 25x25mm, thickness 0.006mm, as rolled, 99.9%
Rhodium, wire reel, 0.05m, diameter 0.25mm, hard, 99.9%
Rhodium, foil, light tested, 25x25mm, thickness 0.075mm, as rolled, 99.9%
Rhodium, microfoil, disks, 25mm, thinness 0.1μm, specific density 124μg/cm2, permanent mylar 3.5μm support, 99.9%
Rhodium, foil, not light tested, 25x25mm, thickness 0.001mm, permanent polyester support, 99.85%
Rhodium, foil, not light tested, 50x50mm, thickness 0.00075mm, permanent polyester support, 99.85%
Rhodium, foil, 25x25mm, thickness 0.125mm, as rolled, 99.9%
Rhodium, wire reel, 0.05m, diameter 0.5mm, as drawn, 99.9%
Rhodium, foil, not light tested, 50x50mm, thickness 0.001mm, permanent polyester support, 99.85%
Rhodium, wire reel, 0.2m, diameter 0.25mm, hard, 99.9%
Rhodium, wire reel, 0.2m, diameter 0.5mm, as drawn, 99.9%
Rhodium, wire reel, 0.5m, diameter 0.12mm, as drawn, 99.9%
Rhodium, wire reel, 0.5m, diameter 0.25mm, hard, 99.9%
Rhodium, foil, not light tested, 50x50mm, thickness 0.00025mm, permanent polyester support, 99.9%