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

Asymmetric synthesis of alpha-branched primary amines on solid support via novel hydrazine resins.

[reaction: see text]. Two novel chiral hydrazine resins for asymmetric solid-phase synthesis have been developed. The enantiopure beta-methoxyamino auxiliaries, derived from trans-4-hydroxy-(S)-proline and (R)-leucine, were attached to Merrifield resin and transformed into their corresponding hydrazines. Immobilization of various aldehydes, followed by 1,2-addition of organolithium reagents to the resulting enantiopure hydrazones and reductive cleavage from the solid support, furnished alpha-branched amines, which were isolated as their corresponding amides in good overall yields and enantiomeric excesses of up to 86%.[1]

References

  1. Asymmetric synthesis of alpha-branched primary amines on solid support via novel hydrazine resins. Enders, D., Kirchhoff, J.H., Köbberling, J., Peiffer, T.H. Org. Lett. (2001) [Pubmed]
 
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