Expedient Synthesis of cis- and trans-3-Aminocyclobutanecarboxylic Acids

被引:6
|
作者
Radchenko, Dmytro S.
Tkachenko, Anton
Grygorenko, Oleksandr O. [1 ]
Komarov, Igor V.
机构
[1] Kyiv Natl Taras Shevchenko Univ, Dept Chem, UA-01033 Kiev, Ukraine
关键词
Amino acids; conformational restriction; cyclobutanes; drug design; GABA analogs; AMINO-ACIDS; STEREOSELECTIVE-SYNTHESIS; GABA;
D O I
10.1080/00397911.2010.491595
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
[image omitted] An expedient approach to cis- and trans-3-aminocyclobutanecarboxylic acids was developed starting from 1,1-cyclobutanedicarboxylic acid. Stereochemistry of the title compounds was established by nuclear Overhauser effect spectroscopy experiments.
引用
收藏
页码:1644 / 1649
页数:6
相关论文
共 50 条
  • [41] Stereospecific synthesis of α,ω-cis- and α,ω-trans-disubstituted oxepanes
    Matsumura, R
    Suzuki, T
    Sato, K
    Inotsume, T
    Hagiwara, H
    Hoshi, T
    Kamat, VP
    Ando, M
    TETRAHEDRON LETTERS, 2000, 41 (40) : 7697 - 7700
  • [42] Stereoselective synthesis of cis- and trans-3-fluoro-1-phenylcyclobutyl amine
    Shao, Pencheng P.
    Ye, Feng
    TETRAHEDRON LETTERS, 2008, 49 (22) : 3554 - 3557
  • [43] Enantioselective total synthesis of cis-(+)- and trans-(+)-disparlure
    Garg, Yuvraj
    Tiwari, Anand Kumar
    Pandey, Satyendra Kumar
    TETRAHEDRON LETTERS, 2017, 58 (34) : 3344 - 3346
  • [44] Efficient synthesis of 3-hydroxymethylated cis- and trans-cyclobutane β-amino acids using an intramolecular photocycloaddition strategy
    Mondiere, Aurlie
    Peng, Runhui
    Remuson, Roland
    Aitken, David J.
    TETRAHEDRON, 2008, 64 (06) : 1088 - 1093
  • [45] Stereodivergent synthesis of enantiopure cis- and trans-3-ethyl-4-piperidineacetates
    Amat, M
    Pérez, M
    Llor, N
    Bosch, J
    ORGANIC LETTERS, 2002, 4 (16) : 2787 - 2790
  • [46] Novel strategies for the synthesis of peptides containing cis- or trans-beta-aminocyclopropane-carboxylic acids
    Bubert, C
    Cabrele, C
    Reiser, O
    SYNLETT, 1997, (07) : 827 - &
  • [47] SYNTHESIS OF CIS- AND TRANS-3-HYDROXY-L-PROLINE, 2 NEW AMINO ACIDS FROM ANTIBIOTIC TELOMYCIN
    SHEEHAN, JC
    WHITNEY, JG
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1963, 85 (23) : 3863 - &
  • [48] STEREIOSOMERISM .2. SYNTHESIS OF SOME CIS- + TRANS-1,3-CYCLOPENTANEDIALKANOIC ACIDS
    WESTMAN, TL
    KOBER, AE
    JOURNAL OF ORGANIC CHEMISTRY, 1964, 29 (08): : 2448 - &
  • [49] An expedient synthesis of cis/trans-1,3-disubstituted cyclobutanols
    Calad, Stacie
    Mans, Douglas
    Morin, Justin-Alexander
    O'Neill-Slawecki, Stacy
    Sisko, Joseph
    TETRAHEDRON LETTERS, 2011, 52 (32) : 4207 - 4210
  • [50] ELECTROLYTIC DECARBOXYLATION OF CIS- AND TRANS-BICYCLO[3.1.0]HEXANE-3-CARBOXYLIC ACIDS
    GASSMAN, PG
    ZALAR, FV
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1966, 88 (10) : 2252 - &