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http://dx.doi.org/10.5012/bkcs.2009.30.5.1003

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)
Publication Information
Bulletin of the Korean Chemical Society / v.30, no.5, 2009 , pp. 1003-1008 More about this Journal
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.
Keywords
Asymmetric synthesis; Amino alcohols; Dihydroxylations; OBO ester;
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