Highly Enantioselective Copper(I)−Fesulphos-Catalyzed 1,3-Dipolar Cycloaddition of Azomethine Ylides
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- 3 November 2005
- journal article
- Published by American Chemical Society (ACS) in Journal of the American Chemical Society
- Vol. 127 (47), 16394-16395
- https://doi.org/10.1021/ja0552186
Abstract
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.This publication has 16 references indexed in Scilit:
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