Cu-Catalyzed Asymmetric 1,3-Dipolar Cycloaddition of Azomethine Ylides with β-Phenylsulfonyl Enones. Ligand Controlled Diastereoselectivity Reversal
The Journal of Organic ChemistryPublished 3 December 2009
Rocío Robles‐Machín, María González‐Esguevillas, Javier Adrio, Juan C. Carretero
Citations71
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TL;DR
A catalytic asymmetric procedure for the 1,3-dipolar cycloaddition of (E)-beta-phenylsulfonyl enones with azomethine ylides to provide highly functionalized pyrrolidine derivatives is described and a switch from endo to exo selectivity was observed when Segphos or DTBM-Segphos ligand was used.
Abstract
A catalytic asymmetric procedure for the 1,3-dipolar cycloaddition of (E)-beta-phenylsulfonyl enones with azomethine ylides to provide highly functionalized pyrrolidine derivatives is described. In the presence of chiral Cu(I)-Segphos catalysts the adducts were obtained with high regio-, diastereo-, and enantioselectivity. Interestingly, a switch from endo to exo selectivity was observed when Segphos or DTBM-Segphos ligand was used.
Keywords
Chemistry
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