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

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...

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Bibliographic Details
Published in:Bulletin of the Korean Chemical Society 2009, Vol.30 (5), p.1003-1008
Main Authors: Jeon, Jong-Ho, Kim, So-Hee, Lee, Jong-Hyup, Oh, Joon-Seok, Park, Doh-Yeon, Kim, Young-Gyu
Format: Article
Language:Korean
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Summary: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.
ISSN:0253-2964
1229-5949