1-(2′,3′,4′,6′-Tetra-O-benzyl-α-d- glucopyranosyl)-2-propene 1a and 1-(2′,3′,4′,6′-tetra-O- benzyl-β-d-glucopyranosyl)-2-propene 1b were hydroformylated at different temperatures affording linear and branched aldehydes in either a 1:1 or 2:1 regioisomeric ratio, depending on the stereochemistry of the starting substrate. The diastereoisomeric ratio of the branched isomer depended on the reaction temperature as well as the alkene structure, the highest value (85:15) being obtained in the case of hydroformylation of the α-isomer at 0°C.

Lazzaroni, R., Rocchiccioli, S., Iuliano, A., Cipolla, L., Nicotra, F. (2005). A New Case of 1,3-Asymmetric Induction in the Rhodium-Catalyzed Hydroformylation of an Allylic Double Bond using Perbenzylated C-glucosides as Chiral Directors. TETRAHEDRON-ASYMMETRY, 16(22), 3661-3666 [10.1016/j.tetasy.2005.09.030].

A New Case of 1,3-Asymmetric Induction in the Rhodium-Catalyzed Hydroformylation of an Allylic Double Bond using Perbenzylated C-glucosides as Chiral Directors

Cipolla, LF;Nicotra, F
2005

Abstract

1-(2′,3′,4′,6′-Tetra-O-benzyl-α-d- glucopyranosyl)-2-propene 1a and 1-(2′,3′,4′,6′-tetra-O- benzyl-β-d-glucopyranosyl)-2-propene 1b were hydroformylated at different temperatures affording linear and branched aldehydes in either a 1:1 or 2:1 regioisomeric ratio, depending on the stereochemistry of the starting substrate. The diastereoisomeric ratio of the branched isomer depended on the reaction temperature as well as the alkene structure, the highest value (85:15) being obtained in the case of hydroformylation of the α-isomer at 0°C.
Articolo in rivista - Articolo scientifico
aldehyde derivative; alkene derivative; allyl compound; benzyl derivative; glucose derivative; glucoside; rhodium
English
2005
16
22
3661
3666
none
Lazzaroni, R., Rocchiccioli, S., Iuliano, A., Cipolla, L., Nicotra, F. (2005). A New Case of 1,3-Asymmetric Induction in the Rhodium-Catalyzed Hydroformylation of an Allylic Double Bond using Perbenzylated C-glucosides as Chiral Directors. TETRAHEDRON-ASYMMETRY, 16(22), 3661-3666 [10.1016/j.tetasy.2005.09.030].
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Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/10281/14434
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