Synthesis of (+)-(1S,2R) and (-)-(1R,2S)-2-aminocyclobutane-1-carboxylic acids

被引:23
|
作者
Gauzy, C [1 ]
Pereira, E [1 ]
Faure, S [1 ]
Aitken, DJ [1 ]
机构
[1] Univ Clermont Ferrand, Dept Chim, Lab SEESIB CNRS, F-63177 Clermont Ferrand, France
关键词
beta-amino acid; cyclobutane; stereoselective synthesis; 2+2] photocycloaddition reaction;
D O I
10.1016/j.tetlet.2004.07.110
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
(+)-(I S,2R) and (-)-(I R,2S)-2-aminocyclobutane-1-carboxylic acids have been prepared in >97% ee and in 33% and 20% overall yields starting from a single, chiral, bicyclic compound perceived as a chiral uracil equivalent. Construction of the cyclobutane ring is achieved via a [2+2] photocycloaddition reaction of this chiral precursor with ethylene. (C) 2004 Elsevier Ltd. All rights reserved.
引用
收藏
页码:7095 / 7097
页数:3
相关论文
共 50 条
  • [1] Folding and self-assembling with β-oligomers based on (1R,2S)-2-aminocyclobutane-1-carboxylic acid
    Torres, Elisabeth
    Gorrea, Esther
    Burusco, Kepa K.
    Da Silva, Eric
    Nolis, Pau
    Rua, Federico
    Boussert, Stephanie
    Diez-Perez, Ismael
    Dannenberg, Samantha
    Izquierdo, Sandra
    Giralt, Ernest
    Jaime, Carlos
    Branchadell, Vicenc
    Ortuno, Rosa M.
    [J]. ORGANIC & BIOMOLECULAR CHEMISTRY, 2010, 8 (03) : 564 - 575
  • [2] Enantioselective synthesis of (1R,2R)- and (1S,2S)-2-nitroxycyclohexan-1-ols
    Basavaiah, D
    Pandiaraju, S
    Muthukumaran, K
    [J]. TETRAHEDRON-ASYMMETRY, 1996, 7 (01) : 13 - 16
  • [3] ENANTIOSELECTIVE SYNTHESIS OF (1R,2S) AND (1S,2S) DEHYDROCORONAMIC ACIDS
    FLICHE, C
    BRAUN, J
    LEGOFFIC, F
    [J]. SYNTHETIC COMMUNICATIONS, 1994, 24 (20) : 2873 - 2876
  • [4] CHEMICAL SYNTHESIS OF THE (1R,2S) AND (1S,2R) ARENE OXIDE METABOLITES OF ACRIDINE
    BOYD, DR
    DORRITY, MRJ
    HAMILTON, L
    MALONE, JF
    SMITH, A
    [J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1994, (19): : 2711 - 2714
  • [5] An easy entry to (1S, 2S) and (1R, 2R)-threo-ifenprodil
    Mantegani, S
    Arlandini, E
    Brambilla, E
    Cremonesi, P
    Varasi, M
    [J]. SYNTHETIC COMMUNICATIONS, 2000, 30 (19) : 3543 - 3553
  • [6] Enzymatic preparation of (1S,2R)- and (1R,2S)-stereoisomers of 2-halocycloalkanols
    Kolodiazhna, Olga O.
    Kolodiazhna, Anastasy O.
    Kolodiazhnyi, Oleg I.
    [J]. TETRAHEDRON-ASYMMETRY, 2013, 24 (01) : 37 - 42
  • [7] A short synthesis of (1S,2R) and (1R,2R)-[1-H-2]-glycerols
    Nieschalk, J
    OHagan, D
    [J]. TETRAHEDRON-ASYMMETRY, 1997, 8 (14) : 2325 - 2330
  • [8] Synthesis of (1S,2S)- and (1R,2R)-1-amino-2-methylcyclopropane-phosphonic acids from racemic methylcyclopropanone acetal
    Tesson, N
    Dorigneux, B
    Fadel, A
    [J]. TETRAHEDRON-ASYMMETRY, 2002, 13 (20) : 2267 - 2276
  • [9] Synthesis of enantiomeric diethyl (1R,2R)- and (1S,2R)-1,2,3-trihydroxypropylphosphonates
    Wróblewski, AE
    Balcerzak, KB
    [J]. TETRAHEDRON, 1998, 54 (24) : 6833 - 6840
  • [10] Resolution of (1R,2R)- and (1S,2S)-cyclic constrained phenylalanine analogues (c6Phe).: Conformations of (1R,2R)- and (1S,2S)-c6Phe containing peptides
    Avenoza, A
    Busto, JH
    Cativiela, C
    Peregrina, JM
    Rodríguez, F
    [J]. TETRAHEDRON, 1998, 54 (38) : 11659 - 11674