Optically pure chloromethyloxazolines have been prepared, lithiated and then reacted with benzophenone to famish stereoselectively oxazolinyl oxiranes and formyl oxiranes. The stereoselection observed has been related to the geometry of the intermediate lithium azaenolates. Calculations have been carried out in order to evaluate the relative stability of the E and Z forms of the lithium azaenolates. The reaction of a lithium azaenolate with other ketones leading to oxazolinyl epoxides is also reported. (C) 2001 Elsevier Science Ltd. All rights reserved

Florio, S., Capriati, V., Luisi, R., Abbotto, A., & Pippel, D.J. (2001). On the coupling reaction of lithium azaenolates of chiral oxazolines with carbonyl compounds. TETRAHEDRON, 57(31), 6775-6786 [10.1016/S0040-4020(01)00611-1].

On the coupling reaction of lithium azaenolates of chiral oxazolines with carbonyl compounds

ABBOTTO, ALESSANDRO;
2001

Abstract

Optically pure chloromethyloxazolines have been prepared, lithiated and then reacted with benzophenone to famish stereoselectively oxazolinyl oxiranes and formyl oxiranes. The stereoselection observed has been related to the geometry of the intermediate lithium azaenolates. Calculations have been carried out in order to evaluate the relative stability of the E and Z forms of the lithium azaenolates. The reaction of a lithium azaenolate with other ketones leading to oxazolinyl epoxides is also reported. (C) 2001 Elsevier Science Ltd. All rights reserved
No
Articolo in rivista - Articolo scientifico
Scientifica
lithium and compounds; enolates; oxazolines; epoxides; computer-assisted methods; Asymmetric-Synthesis; Condensation; 2-Oxazolines; Alkylation; Efficient; Oxiranes; Alcohols;Reagents; Acids
English
6775
6786
12
Florio, S., Capriati, V., Luisi, R., Abbotto, A., & Pippel, D.J. (2001). On the coupling reaction of lithium azaenolates of chiral oxazolines with carbonyl compounds. TETRAHEDRON, 57(31), 6775-6786 [10.1016/S0040-4020(01)00611-1].
Florio, S; Capriati, V; Luisi, R; Abbotto, A; Pippel, D
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Utilizza questo identificativo per citare o creare un link a questo documento: http://hdl.handle.net/10281/128584
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