Organocatalytic synthesis of β-alkylaspartates via β-lactone ring opening

被引:13
作者
Armstrong, Alan [1 ]
Geldart, Stephen P. [1 ]
Jenner, Chloe R. [1 ]
Scutt, James N. [1 ]
机构
[1] Univ London Imperial Coll Sci & Technol, Dept Chem, London SW7 2AZ, England
关键词
D O I
10.1021/jo701461t
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
[GRAPHICS] Cinchona alkaloid-catalyzed reaction of ethyl glyoxylate with substituted ketenes, formed in situ, gives disubstituted beta-lactones in moderate yield and high enantiomeric excess. Subsequent azide ring opening, reduction, and ester hydrolysis allows access to chiral beta-alkyl aspartates.
引用
收藏
页码:8091 / 8094
页数:4
相关论文
共 23 条
  • [1] Total synthesis of (+)-belactosin A
    Armstrong, A
    Scutt, JN
    [J]. CHEMICAL COMMUNICATIONS, 2004, (05) : 510 - 511
  • [2] Stereocontrolled synthesis of 3-(trans-2-aminocyclopropyl)alanine, a key component of belactosin A
    Armstrong, A
    Scutt, JN
    [J]. ORGANIC LETTERS, 2003, 5 (13) : 2331 - 2334
  • [3] NON-PROTEINOGENIC AMINO-ACID SYNTHESIS - THE BETA-ANION DERIVED FROM ASPARTIC-ACID, AND ITS APPLICATION TO ALPHA-AMINO-ACID SYNTHESIS
    BALDWIN, JE
    MOLONEY, MG
    NORTH, M
    [J]. TETRAHEDRON, 1989, 45 (19) : 6309 - 6318
  • [4] ASYMMETRIC CATALYTIC SYNTHESIS OF BETA-BRANCHED AMINO-ACIDS VIA HIGHLY ENANTIOSELECTIVE HYDROGENATION REACTIONS
    BURK, MJ
    GROSS, MF
    MARTINEZ, JP
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1995, 117 (36) : 9375 - 9376
  • [5] Formation of disubstituted β-lactones using bifunctional catalysis
    Calter, MA
    Tretyak, OA
    Flaschenriem, C
    [J]. ORGANIC LETTERS, 2005, 7 (09) : 1809 - 1812
  • [6] Catalytic, asymmetric dimerization of methylketene
    Calter, MA
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (23) : 8006 - 8007
  • [7] Intramolecular, nucleophile-catalyzed aldol-lactonization (NCAL) reactions:: Catalytic, asymmetric synthesis of bicyclic β-lactones
    Cortez, GS
    Tennyson, RL
    Romo, D
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2001, 123 (32) : 7945 - 7946
  • [8] The substituted aspartate analogue L-β-threo-benzyl-aspartate preferentially inhibits the neuronal excitatory amino acid transporter EAAT3
    Esslinger, CS
    Agarwal, S
    Gerdes, J
    Wilson, PA
    Davis, ES
    Awes, AN
    O'Brien, E
    Mavencamp, T
    Koch, HP
    Poulsen, DJ
    Rhoderick, JF
    Chamberlin, AR
    Kavanaugh, MP
    Bridges, RJ
    [J]. NEUROPHARMACOLOGY, 2005, 49 (06) : 850 - 861
  • [9] C2-symmetric Cu(II) complexes as chiral Lewis acids.: Catalytic, enantioselective cycloadditions of silyl ketenes
    Evans, DA
    Janey, JM
    [J]. ORGANIC LETTERS, 2001, 3 (13) : 2125 - 2128
  • [10] A multistage, one-pot procedure mediated by a single catalyst:: A new approach to the catalytic asymmetric synthesis of β-amino acids
    Hafez, AM
    Dudding, T
    Wagerle, TR
    Shah, MH
    Taggi, AE
    Lectka, T
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2003, 68 (15) : 5819 - 5825