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 (2011). A New Robust and Efficient Ion-Tagged Proline Catalyst Carrying an Amide Spacer, for the Asymmetric Aldol Reaction. ADVANCED SYNTHESIS & CATALYSIS, 353, 3234-3240 [10.1002/adsc.201100595].

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.
2011
E. Montroni, S. P. Sanap, M. Lombardo, A. Quintavalla, C. Trombini, D. D. Dhavale (2011). A New Robust and Efficient Ion-Tagged Proline Catalyst Carrying an Amide Spacer, for the Asymmetric Aldol Reaction. ADVANCED SYNTHESIS & CATALYSIS, 353, 3234-3240 [10.1002/adsc.201100595].
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: https://hdl.handle.net/11585/107683
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