Highly Enantioselective Copper(I)−Fesulphos-Catalyzed 1,3-Dipolar Cycloaddition of Azomethine Ylides

• Published in: Journal of the American Chemical Society Vol. 127; no. 47; pp. 16394 - 16395
• Main Authors: Cabrera, Silvia, Arrayás, Ramón Gómez, Carretero, Juan C
• Format: Journal Article
• Language: English
• Published: WASHINGTON American Chemical Society 30.11.2005; Amer Chemical Soc
• Subjects: Chemical reactivity; Chemistry; Chemistry, Multidisciplinary; Exact sciences and technology; Organic chemistry; Physical Sciences; Reactivity and mechanisms; Science & Technology; PROLINE DERIVATIVES; ALKENES; ORIGINS; NITRONES; LIGANDS; 1-PHOSPHINO-2-SULFENYLFERROCENES; CATALYZED ALLYLIC SUBSTITUTIONS; COMPLEXES; STEPWISE; CHIRAL CATALYSTS; 1,3-Dipolar cycloaddition; Five membered ring; Catalytic reaction; Enantioselectivity; Nitrogen heterocycle; Catalyst selectivity; Organic ligand; Transition metal Complexes; Complex catalyst; Experimental study; Copper Complexes; Azomethine ylide; Asymmetric reaction; Catalyst activity
• ISSN: 0002-7863; 1520-5126
• DOI: 10.1021/ja0552186

The catalyst system formed by Cu(CH3CN)4ClO4 and the planar chiral P,S-ligand Fesulphos behaves as a very efficient chiral Lewis acid in the catalytic asymmetric 1,3-dipolar cycloaddition of azomethine ylides. This catalyst shows a remarkable reactivity at low catalyst loading (0.5−3 mol %), affording in good yields the endo adducts with exceptional levels of enantioselectivity (up to >99% ee). This catalytic asymmetric procedure has a broad structural scope with regard to both azomethine and dipolarophile substitution. The first examples of catalytic asymmetric 1,3-dipolar cycloaddition with ketimine-derived azomethines are reported.