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

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

Journal Name: Letters in Organic Chemistry

Volume 4 , Issue 6 , 2007

Become EABM
Become Reviewer

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

Rights & PermissionsPrintExport Cite as

Article Details

VOLUME: 4
ISSUE: 6
Year: 2007
Page: [388 - 392]
Pages: 5
DOI: 10.2174/157017807781467623
Price: $65

Article Metrics

PDF: 4