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

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

Volume: 4 Issue: 6

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

Affiliation:

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

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.

Cite this article as:

Roberta Settambolo , Silvia Rocchiccioli , Gloria Uccello-Barretta and Raffaello Lazzaroni , Chiral N-Allylpyrroles as Versatile Substrates Under Rhodium-Catalyzed Hydroformylation: Good Regio- and Diastereo-Selectivity at Room Temperature and High Pressure, Letters in Organic Chemistry 2007; 4 (6) . https://dx.doi.org/10.2174/157017807781467623