Application of modular nucleophilic glycine equivalents for truly practical asymmetric synthesis of β-substituted pyroglutamic acids

被引：75
作者：
Soloshonok, VA [1 ]
Ueki, H
Ellis, TK
Yamada, T
Ohfune, Y
机构：
[1] Univ Oklahoma, Dept Chem & Biochem, Norman, OK 73019 USA
[2] Osaka City Univ, Grad Sch Sci, Dept Mat Sci, Osaka 5588585, Japan
来源：
TETRAHEDRON LETTERS | 2005年 / 46卷 / 07期
关键词：
glycine equivalents; Michael additions; asymmetric synthesis; amino acids;
D O I：
10.1016/j.tetlet.2004.12.093
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A new series of achiral glycine equivalents have been evaluated with respect to their synthetic utility for the production of beta-substituted pyroglutamic acid derivatives. Among them, the piperidine-de rived complex was found to be a superior glycine derivative for the Michael additions with various (R)-N-(E-enoyl)-4-phenyl-1,3-oxazolidin-2-ones representing a general and practical synthesis of sterically constrained beta-substituted pyroglutamic acids. In particular, application of complex allowed for the first time preparation of the corresponding isopropyl derivatives thus increasing the synthetic efficiency and expanding generality these Michael addition reactions. (C) 2004 Elsevier Ltd. All rights reserved.
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收藏
页码：1107 / 1110
页数：4
相关论文
共 35 条
  • [1] Abellán T, 2000, EUR J ORG CHEM, V2000, P2689
  • [2] BARRETT GC, 1998, CHEM BIOCHEMISTRY AM
  • [3] Beller M, 2000, ANGEW CHEM INT EDIT, V39, P1010, DOI 10.1002/(SICI)1521-3773(20000317)39:6<1010::AID-ANIE1010>3.0.CO
  • [4] 2-P
  • [5] Synthesis of α-amino acids via asymmetric phase transfer-catalyzed alkylation of achiral nickel(II) complexes of glycine-derived Schiff bases
    Belokon, YN
    Bespalova, NB
    Churkina, TD
    Císarová, I
    Ezernitskaya, MG
    Harutyunyan, SR
    Hrdina, R
    Kagan, HB
    Kocovsky, P
    Kochetkov, KA
    Larionov, OV
    Lyssenko, KA
    North, M
    Polásek, M
    Peregudov, AS
    Prisyazhnyuk, VV
    Vyskocil, S
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (42) : 12860 - 12871
  • [6] Industrial methods for the production of optically active intermediates
    Breuer, M
    Ditrich, K
    Habicher, T
    Hauer, B
    Kesseler, M
    Stürmer, R
    Zelinski, T
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2004, 43 (07) : 788 - 824
  • [7] Stereoselective synthesis of quaternary α-amino acids.: Part 2.: Cyclic compounds
    Cativiela, C
    Díaz-de-Villegas, MD
    [J]. TETRAHEDRON-ASYMMETRY, 2000, 11 (03) : 645 - 732
  • [8] Stereoselective synthesis of quaternary α-amino acids.: Part 1:: Acyclic compounds
    Cativiela, C
    Diaz-de-Villegas, MD
    [J]. TETRAHEDRON-ASYMMETRY, 1998, 9 (20) : 3517 - 3599
  • [9] DEGRADO WF, 2001, CHEM REV, P101
  • [10] RECENT DEVELOPMENTS IN THE STEREOSELECTIVE SYNTHESIS OF ALPHA-AMINO-ACIDS
    DUTHALER, RO
    [J]. TETRAHEDRON, 1994, 50 (06) : 1539 - 1650
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