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Diastereoselective Cycloaddition of N-Lithiated Azomethine Ylides to (E)-alpha,beta-Unsaturated Esters Bearing a C2-Symmetric Imidazolidine Chiral Controller
The 1,3-dipolar cycloaddition of N-metalated ylides to chiral (E)-3-(1,3-disubstituted 4,5-diphenylimidazolidin-2-yl)propenoates proceeded highly diastereoselectively.The previously unknown absolute configuration of optically pure 1,2-dianilino-1,2-diphenylethane was determined from the absolute configuration of the cycloadducts.What diastereotopic olefin face of the alpha,beta-unsaturated ester was attacked by the ylide was found to depend dramatically upon the nature of N substituents of the chiral controller as well as upon the bulkiness of the ester moiety of the ylide.
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Reference£º
Metal catalyst and ligand design,
Ligand Template Strategies for Catalyst Encapsulation – NCBI