A series of new chiral oxazoline-1,3-dithianes has been easily synthesized and used as ligands for asymmetric catalysis. The conjugate addition of Et2Zn to enones resulted in ees of up to 69%, whereas the Pd-catalyzed allylic alkylation led to the expected products in almost quantitative yields and up to 90% enantioselectivity. The ligand's conformation has been explored using a combination of X-ray and NMR measurements, indicating the presence of a remarkable anomeric effect, which accounts for the preference of the oxazoline ring for the axial location.

Chiral oxazoline-1,3-dithianes: new effective nitrogen–sulfur donating ligands in asymmetric catalysis / Capitò, Elena; Bernardi, Luca; Comes Franchini, Mauro; Fini, Francesco; Fochi, Mariafrancesca; Pollicino, Salvatore; Ricci, Alfredo. - In: TETRAHEDRON-ASYMMETRY. - ISSN 0957-4166. - STAMPA. - 16:(2005), pp. 3232-3240. [10.1016/j.tetasy.2005.08.043]

Chiral oxazoline-1,3-dithianes: new effective nitrogen–sulfur donating ligands in asymmetric catalysis

FINI, Francesco;
2005

Abstract

A series of new chiral oxazoline-1,3-dithianes has been easily synthesized and used as ligands for asymmetric catalysis. The conjugate addition of Et2Zn to enones resulted in ees of up to 69%, whereas the Pd-catalyzed allylic alkylation led to the expected products in almost quantitative yields and up to 90% enantioselectivity. The ligand's conformation has been explored using a combination of X-ray and NMR measurements, indicating the presence of a remarkable anomeric effect, which accounts for the preference of the oxazoline ring for the axial location.
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Chiral oxazoline-1,3-dithianes: new effective nitrogen–sulfur donating ligands in asymmetric catalysis / Capitò, Elena; Bernardi, Luca; Comes Franchini, Mauro; Fini, Francesco; Fochi, Mariafrancesca; Pollicino, Salvatore; Ricci, Alfredo. - In: TETRAHEDRON-ASYMMETRY. - ISSN 0957-4166. - STAMPA. - 16:(2005), pp. 3232-3240. [10.1016/j.tetasy.2005.08.043]
Capitò, Elena; Bernardi, Luca; Comes Franchini, Mauro; Fini, Francesco; Fochi, Mariafrancesca; Pollicino, Salvatore; Ricci, Alfredo
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Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/11380/1122085
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