Enantioselective syntheses of homophenylalanine derivatives via nitrone 1,3-dipolar cycloaddition reactions with styrenes

被引:35
作者
Long, A [1 ]
Baldwin, SW [1 ]
机构
[1] Duke Univ, Dept Chem, Paul M Gross Chem Lab, Durham, NC 27708 USA
基金
美国国家科学基金会;
关键词
D O I
10.1016/S0040-4039(01)00821-8
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A new two-step route to derivatives of homophenylalanine is presented. Cycloaddition of a cyclic nitrone glycine template with various styrene derivatives affords good yields of 5-substituted cycloadducts. One-step hydrogenolysis (three bonds) then affords the optically pure a-amino acids related to homophenylalanine. (C) 2001 Published by Elsevier Science Ltd.
引用
收藏
页码:5343 / 5345
页数:3
相关论文
共 12 条
  • [1] Preparation and evaluation of a cyclic acyl nitrone as a synthon for stereospecific α-amino acid synthesis
    Baldwin, SW
    Young, BG
    McPhail, AT
    [J]. TETRAHEDRON LETTERS, 1998, 39 (38) : 6819 - 6822
  • [2] ENANTIOSELECTIVE SYNTHESIS OF ALPHA-AMINO-ACID DERIVATIVES VIA THE STEREOSELECTIVE ALKYLATION OF A HOMOCHIRAL GLYCINE ENOLATE SYNTHON
    DELLARIA, JF
    SANTARSIERO, BD
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1989, 54 (16) : 3916 - 3926
  • [3] Synthesis of nitrones by methyltrioxorhenium catalyzed direct oxidation of secondary amines
    Goti, A
    Nannelli, L
    [J]. TETRAHEDRON LETTERS, 1996, 37 (33) : 6025 - 6028
  • [4] PRACTICAL ENANTIOSELECTIVE SYNTHESIS OF A HOMOTYROSINE DERIVATIVE AND (R,R)-4-PROPYL-9-HYDROXYNAPHTHOXAZINE, A POTENT DOPAMINE AGONIST
    MELILLO, DG
    LARSEN, RD
    MATHRE, DJ
    SHUKIS, WF
    WOOD, AW
    COLLELUORI, JR
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1987, 52 (23) : 5143 - 5150
  • [5] Synthesis of nitrones using the methyltrioxorhenium hydrogen peroxide system
    Murray, RW
    Iyanar, K
    Chen, JX
    Wearing, JT
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (23) : 8099 - 8102
  • [6] Biochemical characterisation of an aldoxime-forming flavoprotein involved in 2-phenylethylglucosinolate biosynthesis in Brassica species
    Oldfield, MF
    Bennett, RN
    Kiddle, G
    Wallsgrove, RM
    Botting, NP
    [J]. PLANT PHYSIOLOGY AND BIOCHEMISTRY, 1999, 37 (02) : 99 - 108
  • [7] Design, synthesis, and 1,3-dipolar cycloaddition of (5R)- [and (5S)]-5,6-dihydro-5-phenyl-2H-1,4-oxazin-2-one N-oxides as chiral (E)-geometry-fixed α-alkoxycarbonylnitrones
    Tamura, O
    Gotanda, K
    Yoshino, J
    Morita, Y
    Terashima, R
    Kikuchi, M
    Miyawaki, T
    Mita, N
    Yamashita, M
    Ishibashi, H
    Sakamoto, M
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2000, 65 (25) : 8544 - 8551
  • [8] Intermolecular 1,3-dipolar cycloaddition of chiral and geometry fixed alpha-alkoxycarbonylnitrone, 5,6-dihydro-5-phenyl-2H-1,4-oxazin-2-one N-oxide
    Tamura, O
    Gotanda, K
    Terashima, R
    Kikuchi, M
    Miyawaki, T
    Sakamoto, M
    [J]. CHEMICAL COMMUNICATIONS, 1996, (16) : 1861 - 1862
  • [9] Chelation controlled 1,3-dipolar cycloaddition of 5,6-dihydro-5-phenyl-1,4-oxazin-2-one N-oxide with allyl alcohols:: A short-step synthesis of clavalanine intermediate
    Tamura, O
    Kuroki, T
    Sakai, Y
    Takizawa, J
    Yoshino, J
    Morita, Y
    Mita, N
    Gotanda, K
    Sakamoto, M
    [J]. TETRAHEDRON LETTERS, 1999, 40 (05) : 895 - 898
  • [10] TUFARIELLO JJ, 1978, TETRAHEDRON LETT, P4647