Enantioselective amino acid synthesis by chiral phase-transfer catalysis

被引:779
作者
Maruoka, K [1 ]
Ooi, T [1 ]
机构
[1] Kyoto Univ, Grad Sch Sci, Dept Chem, Sakyo Ku, Kyoto 6068502, Japan
关键词
D O I
10.1021/cr020020e
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Enantioselective synthesis of α-amino acids was greatly advanced by the creation of new chiral phase-transfer catalysts, which maximize the characteristic features of the central quaternary ammonium cations. Indeed, such phase-transfer-catalyzed enatioselective syntheses of α-amino acids were very useful in practical synthesis, and their applications were illustrated in numerous papers. This paper describes the enantioselective reactions which clearly demonstrate the high ability and great potential of chiral phase-transfer catalysis to synthesize various types of chiral α-amino acid derivatives.
引用
收藏
页码:3013 / 3028
页数:16
相关论文
共 104 条
  • [1] New chiral alanine template with a 1,2,3,6-tetrahydro-2-pyrazinone structure for the asymmetric synthesis of α-methyl α-amino acids
    Abellán, T
    Nájera, C
    Sansano, JM
    [J]. TETRAHEDRON-ASYMMETRY, 1998, 9 (13) : 2211 - 2214
  • [2] Asymmetric synthesis of α-amino acids from α,β-(Z)-didehydroamino acid derivatives with 1,2,3,6-tetrahydropyrazin-2-one structure
    Abellán, T
    Mancheño, B
    Nájera, C
    Sansano, JM
    [J]. TETRAHEDRON, 2001, 57 (30) : 6627 - 6640
  • [3] [Anonymous], MODERN SYNTHETIC MET
  • [4] Phase-transfer-catalyzed asymmetric Michael reaction using newly-prepared chiral quaternary ammonium salts derived from L-tartrate
    Arai, S
    Tsuji, R
    Nishida, A
    [J]. TETRAHEDRON LETTERS, 2002, 43 (52) : 9535 - 9537
  • [5] Enantiomerically enriched (R)- and (S)-α-methylphenylalanine via asymmetric PTC C-alkylation catalysed by NOBIN
    Belokon', YN
    Kochetkov, KA
    Churkina, TD
    Ikonnikov, NS
    Vyskocil, S
    Kagan, HB
    [J]. TETRAHEDRON-ASYMMETRY, 1999, 10 (09) : 1723 - 1728
  • [6] Asymmetric PTC C-alkylation mediated by TADDOL -: novel route to enantiomerically enriched α-alkyl-α-amino acids
    Belokon, YN
    Kochetkov, KA
    Churkina, TD
    Ikonnikov, NS
    Chesnokov, AA
    Larionov, OV
    Parmár, VS
    Kumar, R
    Kagan, HB
    [J]. TETRAHEDRON-ASYMMETRY, 1998, 9 (05) : 851 - 857
  • [7] Chiral salen-metal complexes as novel catalysts for asymmetric phase transfer alkylations
    Belokon, YN
    North, M
    Kublitski, VS
    Ikonnikov, NS
    Krasik, PE
    Maleev, VI
    [J]. TETRAHEDRON LETTERS, 1999, 40 (33) : 6105 - 6108
  • [8] A practical asymmetric synthesis of α-methyl α-amino acids using a chiral Cu-salen complex as a phase transfer catalyst
    Belokon', YN
    Davies, RG
    North, M
    [J]. TETRAHEDRON LETTERS, 2000, 41 (37) : 7245 - 7248
  • [9] BOCCHI V, 1979, SYNTHESIS-STUTTGART, P957
  • [10] 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