• Title/Summary/Keyword: Asymmetric dihydroxylation

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Osmylated Macroporous Cinchona Alkaloid Resins: Highly Efficient and Recyclable Catalysts for Asymmetric Dihydroxylation of Olefins

  • Park, Yil-Sung;Jo, Cheon-Hee;Choi, Han-Young;Kwon, Eun-Kyung;Song, Choong-Eui
    • Bulletin of the Korean Chemical Society
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    • v.25 no.11
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    • pp.1671-1675
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    • 2004
  • A simple method for simultaneous recovery and reuse of $OsO_4$ and alkaloid ligand in the asymmetric dihydroxylation of olefins has been developed by using macroporous alkaloid resins bearing residual vinyl groups.

Stereocontrolled Dihydroxylation Reactions of Acyclic Allylic Amines (비고리 알릴아민 화합물의 입체선택적 이중알코올화 반응)

  • Jeon, Jongho;Shin, Nara;Kim, Young Gyu
    • Applied Chemistry for Engineering
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    • v.25 no.5
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    • pp.437-446
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    • 2014
  • The dihydroxylation reaction of allylic amines is a facile and useful synthetic method to obtain amino diol structures that are widely found in lots of biologically important natural products. This review will focus on the recent methods of both substrate-controlled and ligand-controlled dihydroxylation reactions of acyclic allylic amines. In addition, several applications of the diastereoselective dihydroxylation methods to asymmetric syntheses of natural products are presented.

Total Synthesis of Azasugar 1,4-Dideoxy-1,4-imino-D-galacitol

  • Sadhu, Partha Sarathi;Santhoshi, Amlipur;Rao, Vaidya Jayathirtha
    • Bulletin of the Korean Chemical Society
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    • v.33 no.11
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    • pp.3554-3558
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    • 2012
  • A new highly stereoselective synthesis of pyrrolidine azasugar 1,4-dideoxy-1,4-imino-D-galacitol is being reported herein. The synthesis was achieved in a linear sequence and inexpensive chiral source (+)-diethyl tartarate was used as the starting material. The key step involved during the synthesis was Pd catalysed amino cyclization of alkenylamine, Bose modified Mitsunobu reaction and Sharpless asymmetric dihydroxylation.

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

  • Jeon, Jong-Ho;Kim, So-Hee;Lee, Jong-Hyup;Oh, Joon-Seok;Park, Doh-Yeon;Kim, Young-Gyu
    • Bulletin of the Korean Chemical Society
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    • v.30 no.5
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    • pp.1003-1008
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    • 2009
  • 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.