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Hoffmann, R. A wiki for the life sciences where authorship matters. Nature Genetics (2008)
 

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Amination of N-aryl prolinol via ring expansion and contraction: application to the chiral ligand for the catalytic asymmetric reaction.

Chiral diaminophosphines 4 were prepared from (S)-prolinol-derived aminophosphine oxide 5 by bromination with ring expansion followed by amination with ring contraction and reduction, using trichlorosilane. In the presence of 4 as a ligand, palladium-catalyzed asymmetric allylic alkylation of 1,3-diphenyl-2-propenyl acetate (11) with a dialkyl malonate-BSA-LiOAc system was successfully carried out with good enantioselectivities (up to 98% ee).[1]

References

  1. Amination of N-aryl prolinol via ring expansion and contraction: application to the chiral ligand for the catalytic asymmetric reaction. Mino, T., Saito, A., Tanaka, Y., Hasegawa, S., Sato, Y., Sakamoto, M., Fujita, T. J. Org. Chem. (2005) [Pubmed]
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