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Highly enantioselective rhodium(I)-catalyzed carbonyl carboacylations initiated by C-C bond activation.
Journal article

Highly enantioselective rhodium(I)-catalyzed carbonyl carboacylations initiated by C-C bond activation.

  • Souillart L Laboratory of Asymmetric Catalysis and Synthesis, EPFL SB ISIC LCSA, BCH 4305, 1015 Lausanne (Switzerland) http://isic.epfl.ch/lcsa.
  • Cramer N
  • 2014-07-22
Published in:
  • Angewandte Chemie (International ed. in English). - 2014
CC activation
acylation
asymmetric catalysis
lactones
rhodium
Acylation
Aldehydes
Alkenes
Catalysis
Ketones
Lactones
Models, Molecular
Rhodium
Stereoisomerism
English The lactone motif is ubiquitous in natural products and pharmaceuticals. The Tishchenko disproportionation of two aldehydes, a carbonyl hydroacylation, is an efficient and atom-economic access to lactones. However, these reaction types are limited to the transfer of a hydride to the accepting carbonyl group. The transfer of alkyl groups enabling the formation of CC bonds during the ester formation would be of significant interest. Reported herein is such asymmetric carbonyl carboacylation of aldehydes and ketones, thus affording complex bicyclic lactones in excellent enantioselectivities. The rhodium(I)-catalyzed transformation is induced by an enantiotopic CC bond activation of a cyclobutanone and the formed rhodacyclic intermediate reacts with aldehyde or ketone groups to give highly functionalized lactones.
Language
  • English
Open access status
closed
Identifiers
Persistent URL
https://fredi.hepvs.ch/global/documents/22235
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