SYNTHESIS OF OXAZOLIDINE DERIVATIVES OF BETA-[3-(ARYLOXY)ARYL]-ALPHA-AMINO ACIDS BY APPLICATION OF THE DIELS-ALDER REACTION

被引：11
|
作者：
OLSEN, RK
FENG, XQ
机构：
[1] Department of Chemistry and Biochemistry, Utah State University Logan
来源：
TETRAHEDRON LETTERS | 1991年 / 32卷 / 41期
关键词：
DIELS-ALDER; ALPHA-AMINO ACIDS; DIARYL ETHER; OXAZOLIDINE; SYNTHESIS;
D O I：
10.1016/S0040-4039(00)93539-1
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
The Diels-Alder reaction has been used to construct the diaryl ether unit in oxazolidine derivatives of beta-[3-(aryloxy)aryl]-alpha-amino acids. Cycloaddition of acetylenic ketone 6 with substituted aryloxy dienes, and subsequent aromatization, provided the title compounds in good yields. Reaction of 6 with Danishefsky's diene furnished optically pure derivatives of L-tyrosine.
引用
收藏
页码：5721 / 5724
页数：4
相关论文
共 50 条
  • [21] One pot imino Diels-Alder reaction for the synthesis of 3-aryl-3,4-dihydrobenzo[f]quinoline derivatives catalyzed by antimony trichloride
    Maiti, Gourhari
    Karmakar, Rajiv
    Kayal, Utpal
    TETRAHEDRON LETTERS, 2013, 54 (23) : 2920 - 2923
  • [22] SIMPLE SYNTHESIS OF 3-ACETYL-2-NORBORNANONE VIA DIELS-ALDER REACTION AND REACTIVITY OF ITS DERIVATIVES
    GOTTSCHALK, FJ
    WEYERSTAHL, P
    CHEMISCHE BERICHTE-RECUEIL, 1980, 113 (02): : 555 - 565
  • [23] Synthesis of Novel Fluoranthene-Based Conformationally Constrained α-Amino Acid Derivatives and Polycyclic Aromatics via the Diels-Alder Reaction
    Kotha, Sambasivarao
    Meshram, Milind
    SYNTHESIS-STUTTGART, 2014, 46 (11): : 1525 - 1531
  • [24] AN EFFICIENT METHOD FOR THE STEREOSELECTIVE SYNTHESIS OF TRICYCLIC COMPOUNDS - THE INTRAMOLECULAR DIELS-ALDER REACTION OF CYCLIC ALPHA,BETA-UNSATURATED CARBOXAMIDES
    TAKEBAYASHI, T
    IWASAWA, N
    MUKAIYAMA, T
    CHEMISTRY LETTERS, 1982, (04) : 579 - 582
  • [25] Diels-Alder cycloadditions of 3-phenylamino-5-bromo-2-pyrone for the synthesis of constrained α-amino acid derivatives
    Kim, WS
    Lee, JH
    Kang, J
    Cho, CG
    TETRAHEDRON LETTERS, 2004, 45 (08) : 1683 - 1687
  • [26] Synthesis of 3-Amino-8-azachromans and 3-Amino-7-azabenzofurans via Inverse Electron Demand Diels-Alder Reaction
    Badarau, Eduard
    Suzenet, Franck
    Finaru, Adriana-Luminita
    Guillaumet, Gerald
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2009, 2009 (21) : 3619 - 3627
  • [27] Synthesis of substituted 1-thiocyanatobutadienes and their application in a Diels-Alder/[3,3] sigmatropic rearrangement tandem reaction
    Lanaspèze, S
    Neier, R
    MONATSHEFTE FUR CHEMIE, 2005, 136 (04): : 597 - 607
  • [28] Synthesis of Substituted 1-Thiocyanatobutadienes and their Application in a Diels-Alder/[3,3] Sigmatropic Rearrangement Tandem Reaction
    Sébastien Lanaspèze
    Reinhard Neier
    Monatshefte für Chemie / Chemical Monthly, 2005, 136 : 597 - 607
  • [29] EFFICIENT ONE POT SYNTHESIS OF CHROMENONAPHTHYRIDINE DERIVATIVES BY CuI/InCl3 CATALYZED AZA DIELS-ALDER REACTION
    Maji, Pradip Kumar
    Mahalanobish, Ayan
    HETEROCYCLES, 2018, 96 (01) : 43 - 49
  • [30] Application of the intramolecular Diels-Alder vinylarene (IMDAV) reaction for the synthesis of benzo-, carbocyclo-, thienothiopheneisoindolecarboxylic acids and its limitations
    Yakovleva, Elizaveta D.
    Shelukho, Evgeniya R.
    Nadirova, Maryana A.
    Erokhin, Pavel P.
    Simakova, Daria N.
    Khrustalev, Victor N.
    Grigoriev, Mikhail S.
    Novikov, Anton P.
    Romanycheva, Anna A.
    Shetnev, Anton A.
    Bychkova, Olga P.
    Trenin, Alexey S.
    Zubkov, Fedor I.
    Zaytsev, Vladimir P.
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2024, 22 (13) : 2643 - 2653
12345