Enantioselective alkylation of alanine-derived imines using quaternary ammonium catalysts.

被引:138
作者
Lygo, B
Crosby, J
Peterson, JA
机构
[1] Univ Salford, Dept Chem & Appl Chem, Salford M5 4WT, Lancs, England
[2] AstraZeneca, Process R&D, Macclesfield SK10 2NA, Cheshire, England
关键词
D O I
10.1016/S0040-4039(99)01836-5
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Application of N-anthracenylmethyl dihydrocinchonidinium bromide as a catalyst for the enantioselective alkylation of a series of alanine-derived imines is reported. Using solid K2CO3/KOH as the stochiometric base such alkylations can be achieved with enantiomeric excesses up to 87% allowing rapid access to alpha,alpha-dialkyl-alpha-amino acid esters. (C) 1999 Published by Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:8671 / 8674
页数:4
相关论文
共 30 条
  • [1] 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
  • [2] 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
  • [3] 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
  • [4] NEW APPROACHES TO THE ASYMMETRIC-SYNTHESIS OF ALPHA-METHYLPHENYLALANINE
    CATIVIELA, C
    DIAZDEVILLEGAS, MD
    GALVEZ, JA
    [J]. TETRAHEDRON-ASYMMETRY, 1994, 5 (02) : 261 - 268
  • [5] Highly enantioselective synthesis of cyclic and functionalized α-amino acids by means of a chiral phase transfer catalyst
    Corey, EJ
    Noe, MC
    Xu, F
    [J]. TETRAHEDRON LETTERS, 1998, 39 (30) : 5347 - 5350
  • [6] A rational approach to catalytic enantioselective enolate alkylation using a structurally rigidified and defined chiral quaternary ammonium salt under phase transfer conditions
    Corey, EJ
    Xu, F
    Noe, MC
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1997, 119 (50) : 12414 - 12415
  • [7] Enantioselective PTC:: Varying the cinchona alkaloid motive
    Dehmlow, EV
    Wagner, S
    Müller, A
    [J]. TETRAHEDRON, 1999, 55 (20) : 6335 - 6346
  • [8] Esikova I.A., 1997, ACS SYM SER, V659, P89
  • [9] Enantioselective synthesis of β-hydroxy-α-amino acid esters by aldol coupling using a chiral quaternary ammonium salt as catalyst
    Horikawa, M
    Busch-Petersen, J
    Corey, EJ
    [J]. TETRAHEDRON LETTERS, 1999, 40 (20) : 3843 - 3846
  • [10] STEREOSELECTIVE SYNTHESIS AND PEPTIDE INCORPORATION OF (S)-ALPHA-AMINO-(2,2'-BIPYRIDINE)-6-PROPANOIC ACID
    IMPERIALI, B
    FISHER, SL
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1992, 57 (02) : 757 - 759