The synthesis of a new, highly efficient cis-ion-tagged catalyst (8a), possessing an amide linkage between the imidazolium tag and the proline ring, is described. This new bench-stable catalyst has been tested in the classic asymmetric aldol condensation between ketones and aldehydes "in the presence" of water, and is proposed as a valuable alternative to the analogous but more sensitive ester cis-2d. Catalyst 8a displayed an excellent efficiency in terms of catalyst loading and stereochemical control.

A New Robust and Efficient Ion-Tagged Proline Catalyst Carrying an Amide Spacer, for the Asymmetric Aldol Reaction

MONTRONI, ELISA;LOMBARDO, MARCO;QUINTAVALLA, ARIANNA;TROMBINI, CLAUDIO;
2011

Abstract

The synthesis of a new, highly efficient cis-ion-tagged catalyst (8a), possessing an amide linkage between the imidazolium tag and the proline ring, is described. This new bench-stable catalyst has been tested in the classic asymmetric aldol condensation between ketones and aldehydes "in the presence" of water, and is proposed as a valuable alternative to the analogous but more sensitive ester cis-2d. Catalyst 8a displayed an excellent efficiency in terms of catalyst loading and stereochemical control.
E. Montroni; S. P. Sanap; M. Lombardo; A. Quintavalla; C. Trombini; D. D. Dhavale
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Utilizza questo identificativo per citare o creare un link a questo documento: http://hdl.handle.net/11585/107683
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