Highly stereoselective allylation of a series of chiral tricarbonylchromium benzaldimine complexes (2a-c) was achieved at -20 degrees C and homoallyl amine complexes (4a-c) were isolated in good yields. In the case of homoallyl amine 4c, obtained in 75% d.e., the degree of stereoselection depends on the catalyst and the reaction conditions. The crystal structure of the major diastereoisomer of racemic 4c was determined by X-ray diffraction, which showed a (S,S) or (R,R) configuration, in agreement with the stereochemical model operating for the ortho-substituted tricarbonylchromium arene complexes. Furthermore, the new tricarbonylchromium complex of N-(2-methoxybenzyliden)diphenyl phosphinamide 3 was prepared. This substrate is a stable analog of the normally unviable ammonia imine. (C) 2000 Elsevier Science S.A. All rights reserved

Maiorana, S., Baldoli, C., Del Buttero, P., Licandro, E., Papagni, A., Lanfranchi, M., et al. (2000). Studies of the stereoselective allylation of chiral benzaldimine chromium tricarbonyl complexes. JOURNAL OF ORGANOMETALLIC CHEMISTRY, 593, 380-387 [10.1016/S0022-328X(99)00601-4].

Studies of the stereoselective allylation of chiral benzaldimine chromium tricarbonyl complexes

PAPAGNI, ANTONIO;
2000

Abstract

Highly stereoselective allylation of a series of chiral tricarbonylchromium benzaldimine complexes (2a-c) was achieved at -20 degrees C and homoallyl amine complexes (4a-c) were isolated in good yields. In the case of homoallyl amine 4c, obtained in 75% d.e., the degree of stereoselection depends on the catalyst and the reaction conditions. The crystal structure of the major diastereoisomer of racemic 4c was determined by X-ray diffraction, which showed a (S,S) or (R,R) configuration, in agreement with the stereochemical model operating for the ortho-substituted tricarbonylchromium arene complexes. Furthermore, the new tricarbonylchromium complex of N-(2-methoxybenzyliden)diphenyl phosphinamide 3 was prepared. This substrate is a stable analog of the normally unviable ammonia imine. (C) 2000 Elsevier Science S.A. All rights reserved
Articolo in rivista - Articolo scientifico
tricarbonylchromium arenes; stereoselective allylation; imines; homoallylamines
English
2000
593
380
387
none
Maiorana, S., Baldoli, C., Del Buttero, P., Licandro, E., Papagni, A., Lanfranchi, M., et al. (2000). Studies of the stereoselective allylation of chiral benzaldimine chromium tricarbonyl complexes. JOURNAL OF ORGANOMETALLIC CHEMISTRY, 593, 380-387 [10.1016/S0022-328X(99)00601-4].
File in questo prodotto:
Non ci sono file associati a questo prodotto.

I documenti in IRIS sono protetti da copyright e tutti i diritti sono riservati, salvo diversa indicazione.

Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/10281/5669
Citazioni
  • Scopus 13
  • ???jsp.display-item.citation.isi??? 14
Social impact