Bulletin of the Korean Chemical Society

Korean Chemical Society (대한화학회)
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Anti-Selective Dihydroxylation Reactions of Monosubstituted and (E)-Ester Conjugated Allylic Amines by Bulky Alkyl Groups

  • Jeon, Jong-Ho (Department of Chemical and Biological Engineering, Seoul National University) ;
  • Kim, So-Hee (Department of Chemical and Biological Engineering, Seoul National University) ;
  • Lee, Jong-Hyup (Department of Chemical and Biological Engineering, Seoul National University) ;
  • Oh, Joon-Seok (Department of Chemical and Biological Engineering, Seoul National University) ;
  • Park, Doh-Yeon (Department of Chemical and Biological Engineering, Seoul National University) ;
  • Kim, Young-Gyu (Department of Chemical and Biological Engineering, Seoul National University)
  • Published : 2009.05.20
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Abstract

The $O_sO_4$-catalyzed dihydroxylations of a monosubstituted allylic amine and $\gamma-amino-\alpha,\;\beta-unsaturated$ (E)-esters with bulky alkyl groups showed a high anti-selectivity. Since the acyclic conformation of N-acyloxy protected allylic amines was efficiently controlled by a bulky t-Bu or OBO ester group, the anti diastereoselectivity of >12.5:1 was obtained without applying a chiral reagent. The synthetic utility of the present method was demonstrated by a stereoselective and efficient synthesis of an $\alpha$-glucosidase inhibitor 15 from commercially available N-Cbz-L-serine 6 in 11 steps and 31% yield.

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References

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