Chemoenzymatic synthesis of N-Boc protected (2S,3R)-3-hydroxy-3-methylproline

被引：7
作者：
Haddad, M [1 ]
Larchevêque, M [1 ]
机构：
[1] Ecole Natl Super Chim Paris, CNRS, Synth Organ Lab, F-75231 Paris, France
来源：
TETRAHEDRON-ASYMMETRY | 2005年 / 16卷 / 13期
关键词：
D O I：
10.1016/j.tetasy.2005.05.030
中图分类号：
O61 [无机化学];
学科分类号：
070301 ; 081704 ;
摘要：
N-Boc protected 3-hydroxy-2-hydroxymetliyl-3-methylpyrrolidine was kinetically resolved by acylation in an organic solvent catalyzed by Pseudomonas fluorescens lipase to give the corresponding acetate and residual diol in 14 E. Further selective oxidation afforded the title compound in high diastereo- and enantioselectivity. (c) 2005 Elsevier Ltd. All rights reserved.
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页码：2243 / 2247
页数：5
相关论文
共 35 条
  • [1] 3-PYRROLIDINONES BY INTRAMOLECULAR CONDENSATION
    BLAKE, J
    RAPOPORT, H
    WILLSON, CD
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1964, 86 (23) : 5293 - &
  • [2] A GREATLY IMPROVED PROCEDURE FOR RUTHENIUM TETRAOXIDE CATALYZED OXIDATIONS OF ORGANIC-COMPOUNDS
    CARLSEN, PHJ
    KATSUKI, T
    MARTIN, VS
    SHARPLESS, KB
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1981, 46 (19) : 3936 - 3938
  • [3] QUANTITATIVE-ANALYSES OF BIOCHEMICAL KINETIC RESOLUTIONS OF ENANTIOMERS
    CHEN, CS
    FUJIMOTO, Y
    GIRDAUKAS, G
    SIH, CJ
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1982, 104 (25) : 7294 - 7299
  • [4] LINEAR OLIGOPEPTIDES .316. CONFORMATIONAL CHARACTERIZATION OF SYNDIOTACTIC HOMO-PEPTIDES FROM C-ALPHA,ALPHA-DISUBSTITUTED GLYCINES
    CRISMA, M
    FORMAGGIO, F
    PANTANO, M
    VALLE, G
    BONORA, GM
    TONIOLO, C
    SCHOEMAKER, HE
    KAMPHUIS, J
    [J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2, 1994, (08): : 1735 - 1742
  • [5] INTRAMOLECULAR HYDROGEN-BONDING IN DERIVATIVES OF BETA-ALANINE AND GAMMA-AMINO BUTYRIC-ACID - MODEL STUDIES FOR THE FOLDING OF UNNATURAL POLYPEPTIDE BACKBONES
    DADO, GP
    GELLMAN, SH
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1994, 116 (03) : 1054 - 1062
  • [6] Asymmetric synthesis of α-amino 1,3-dithioketals from sulfinimines (N-sulfinyl imines).: Synthesis of (2S,3R)-(-)-3-hydroxy-3-methylproline
    Davis, FA
    Ramachandar, T
    Liu, H
    [J]. ORGANIC LETTERS, 2004, 6 (19) : 3393 - 3395
  • [7] Foldamers: A manifesto
    Gellman, SH
    [J]. ACCOUNTS OF CHEMICAL RESEARCH, 1998, 31 (04) : 173 - 180
  • [8] Lipase catalyzed resolution of chiral acids or alcohols using mixed carboxylic-carbonic anhydrides
    GuibeJampel, E
    Chalecki, Z
    Bassir, M
    GeloPujic, M
    [J]. TETRAHEDRON, 1996, 52 (12) : 4397 - 4402
  • [9] Hydroxymethylated cyclic α-amino acid dipeptides by ruthenium ring closing metathesis
    Hammer, K
    Undheim, K
    [J]. TETRAHEDRON-ASYMMETRY, 1998, 9 (13) : 2359 - 2368
  • [10] Total synthesis of (-)-slaframine from (2R,3S)-3-hydroxyproline
    Knight, DW
    Sibley, AW
    [J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1997, (15): : 2179 - 2187
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