Asymmetric addition reaction of phenyllithium to 1,2-ethylenediimine with the aid of a chiral ligand

Article abstract of DOI:10.1248/cpb.45.1705

The reaction of N,N'-bis(4-methoxyphenyl)ethylenediimine with phenyllithium, with the mediation of a chiral ligand, provided the addition products, (1R,2R)-N,N'-bis(4-methoxyphenyl)-1,2-diphenylethanediamine of 67% ee and the meso-product, in a ratio of 41:59. The net reaction involves sequential double additions of phenyllithium. In the first addition a new chiral center is created, but with rather poor selectivity, and in the second addition kinetic discrimination takes place, giving the chiral double addition product.

Full text of DOI:10.1248/cpb.45.1705

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