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

An unusual electronic effect of an aromatic-F in phase-transfer catalysts derived from cinchona-alkaloid.

[structure: see text] Various N-benzylcinchonidinium salts were prepared to study electronic factors in the catalytic enantioselective phase-transfer alkylation of glycine anion equivalent. An ortho-fluoro substituent on the benzyl group in the quaternary ammonium salt dramatically increased the enantioselectivity in the alkylation. O(9)-Allyl-N-2',3',4'-trifluorobenzylhydrocinchonidinium bromide (27), which gave the highest enantioselectivity of the catalysts studied, was used to prepare 12 alpha-alkylated amino acid derivatives in 94 approximately >99% ee.[1]

References

  1. An unusual electronic effect of an aromatic-F in phase-transfer catalysts derived from cinchona-alkaloid. Jew, S.S., Yoo, M.S., Jeong, B.S., Park, I.Y., Park, H.G. Org. Lett. (2002) [Pubmed]
 
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