A practical asymmetric synthesis of α-methyl α-amino acids using a chiral Cu-salen complex as a phase transfer catalyst

被引:76
作者
Belokon', YN
Davies, RG
North, M [1 ]
机构
[1] Kings Coll London, Dept Chem, London WC2R 2LS, England
[2] AN Nesmeyanov Organoelement Cpds Inst, Moscow 117813, Russia
基金
英国工程与自然科学研究理事会;
关键词
phase transfer; catalysis; copper; asymmetric synthesis; amino acid;
D O I
10.1016/S0040-4039(00)01247-8
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The asymmetric C-alkylation of N-benzylidene alanine methyl ester has been achieved using a copper(II) (salen) complex as an asymmetric phase transfer catalyst and provides a practical synthesis of alpha-methyl alpha-amino acids with up to 86% enantiomeric excess. (C) 2000 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:7245 / 7248
页数:4
相关论文
共 33 条
  • [1] New polymer-supported catalysts derived from Cinchona alkaloids:: Their use in the asymmetric Michael reaction
    Alvarez, R
    Hourdin, MA
    Cavé, C
    d'Angelo, J
    Chaminade, P
    [J]. TETRAHEDRON LETTERS, 1999, 40 (39) : 7091 - 7094
  • [2] Asymmetric cyclopropanation reaction under phase-transfer catalyzed conditions
    Arai, S
    Nakayama, K
    Ishida, T
    Shioiri, T
    [J]. TETRAHEDRON LETTERS, 1999, 40 (22) : 4215 - 4218
  • [3] Asymmetric synthesis of α,β-epoxysulfones under phase-transfer catalyzed Darzens reaction
    Arai, S
    Ishida, T
    Shioiri, T
    [J]. TETRAHEDRON LETTERS, 1998, 39 (45) : 8299 - 8302
  • [4] 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
  • [5] 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
  • [6] 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
  • [7] CHIRAL MICHAEL ADDITION - METHYL VINYL KETONE ADDITION CATALYZED BY CINCHONA ALKALOID DERIVATIVES
    CONN, RSE
    LOVELL, AV
    KARADY, S
    WEINSTOCK, LM
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1986, 51 (24) : 4710 - 4711
  • [8] Highly enantioselective phase transfer catalyzed alkylation of a 3-oxygenated propionic ester equivalent; applications and mechanism
    Corey, EJ
    Bo, YX
    Busch-Petersen, J
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1998, 120 (49) : 13000 - 13001
  • [9] 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
  • [10] 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