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Substrate-directed asymmetric induction in the rhodium catalyzed hydroformylation of C-allyl-sugars: The influence of the glycoside-moiety on the selectivity of the reaction

Authors
Journal
Journal of Organometallic Chemistry
0022-328X
Publisher
Elsevier
Publication Date
Volume
691
Issue
19
Identifiers
DOI: 10.1016/j.jorganchem.2006.06.008
Keywords
  • Hydroformylation
  • C-Allylglicosides
  • Asymmetric Induction
  • Rhodium

Abstract

Abstract α- and β-C-allylgalactopyranosides 1c and 1d, α-C-allylazaglucopyranoside 1e and α-C-allylfruttofuranoside 1f were hydroformylated at low temperatures affording a mixture of linear and branched aldehydes in regioisomeric and diastereoisomeric ratios depending on the starting alkene. The results obtained have allowed us to study the influence of the different structural features of the sugar moiety on the regio- and diastereoselectivity of the hydroformylation reaction.

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