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

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, th...

Full description

Saved in:
Bibliographic Details
Published in:Bulletin of the Korean Chemical Society 2009, 30(5), , pp.1003-1008
Main Authors: Jongho Jeon, So-Hee Kim, Jong Hyup Lee, Joon Seok Oh, Doh Yeon Park, 김영규
Format: Article
Language:English
Subjects:
화학
Citations: Items that this one cites
Items that cite this one
Online Access:Get full text
Tags: Add Tag
No Tags, Be the first to tag this record!
Description
Summary: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. KCI Citation Count: 6
ISSN:0253-2964
1229-5949
DOI:10.5012/bkcs.2009.30.5.1003