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Letters in Organic Chemistry

Author(s): Roberta Settambolo, Silvia Rocchiccioli, Gloria Uccello-Barretta and Raffaello Lazzaroni

DOI: 10.2174/157017807781467623

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Chiral N-Allylpyrroles as Versatile Substrates Under Rhodium-Catalyzed Hydroformylation: Good Regio- and Diastereo-Selectivity at Room Temperature and High Pressure

Page: [388 - 392] Pages: 5

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Abstract

The chiral (S)-3-alkyl-3-(pyrrol-1-yl)prop-1-enes 1a-c were hydroformylated at 20°C and high pressure (100 atm) giving the branched aldehydes 2-methyl-3-(pyrrol-1-yl)alkanales (2+2) with a good regio-selectivity and a high diastereomeric excess (2/2 up to 90:10). The absolute configuration of the diastereomers was assigned via NMR measurements, 2S,3S being the predominant one.

Keywords: Hydroformylation, rhodium catalyst, pyrrolyl olefins, pyrrolylalkanales, 1,2-substrate-induced diastereoselectivity