Atroposelective alkylation

Chelation-assisted C-H/olefin coupling can be applied to the atroposelective alkylation of biaryl compounds. The reaction of 2-(l-naphthyl)-3-methylpyri-dine with ethylene using [RhCl(coe)2]2 where coe is cyclooctene, and PCy3 results in the formation of an ethylation product in 92% yield (Eq. 21) [20]. In place of the PCy3 ligand, the use of (R) - (1 - [ (S) - 2- diphenylphosphino ] ferro-cenyl)ethyl methyl ether [(R),(S)-PPFOMe] leads to the atropselective alkyla-... 

Kakiuchi et al. succeeded in the atroposelective alkylation of the 2-(l-naphthyl)-3-methylpyridine with ethylene catalyzed by [RhCl(coe)2]2 and a chiral ferrocenyl phosphine (R) or (S)-PPFOMe (Figure 15). This is a kind of dynamic kinetic resolution. The pelds were moderate with fair to good ees (00TA2647). 

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See also in sourсe #XX -- [ ]

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