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Bulletin of the Korean Chemical Society (BKCS)

ISSN 0253-2964(Print)
ISSN 1229-5949(Online)
Volume 30, Number 5
BKCSDE 30(5)
May 20, 2009 

Anti-Selective Dihydroxylation Reactions of Monosubstituted and (E)-Ester Conjugated Allylic Amines by Bulky Alkyl Groups
Jongho Jeon, So Hee Kim, Jong Hyup Lee, Joon Seok Oh, Doh Yeon Park, Young Gyu Kim*
Asymmetric synthesis, Amino alcohols, Dihydroxylations, OBO ester
The OsO4-catalyzed dihydroxylations of a monosubstituted allylic amine and γ-amino-α,β-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 α-glucosidase inhibitor 15 from commercially available N-Cbz-L-serine 6 in 11 steps and 31% yield.
1003 - 1008
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