Synthesis of chiral cyclic nitrones via a nitrosoketene intermediate and their use for the complete EPC synthesis of nonproteinogenic amino acids

被引：45
|
作者：
Katagiri, N
Okada, M
Kaneko, C
机构：
[1] TOHOKU UNIV,INST PHARMACEUT,SENDAI,MIYAGI 98077,JAPAN
[2] YAMANOUCHI PHARMACEUT CO LTD,TSUKUBA RES LABS,TSUKUBA,IBARAKI 305,JAPAN
来源：
TETRAHEDRON LETTERS | 1996年 / 37卷 / 11期
关键词：
D O I：
10.1016/0040-4039(96)00122-0
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
New cyclic chiral nitrones constituting tw diastereomers were synthesized by the reaction of isonitroso Meldrum's acid with l-menthone via a nitrosoketene intermediate. Both nitrones reacted with allyltrimethylsilane diastereoselectively to give the corresponding isoxazolidine derivatives as sole products, which were converted to (S)- and (R)- allylglycines in ca. 100% ee, respectively.
引用
收藏
页码：1801 / 1804
页数：4
相关论文
共 50 条
  • [1] Formation of functional cyclic nitrones via a new reaction intermediate, nitrosoketene and its development for the synthesis of nonproteinogenic amino acids
    Katagiri, N
    Ishikura, M
    Kaneko, C
    JOURNAL OF SYNTHETIC ORGANIC CHEMISTRY JAPAN, 1999, 57 (02) : 116 - 126
  • [2] A NOVEL SYNTHESIS OF CYCLIC NITRONES VIA A NITROSOKETENE INTERMEDIATE
    KATAGIRI, N
    KURIMOTO, A
    YAMADA, A
    SATO, H
    KATSUHARA, T
    TAKAGI, K
    KANEKO, C
    JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1994, (03) : 281 - 282
  • [3] A NEW SYNTHESIS OF HIGHLY FUNCTIONAL NITRONES THROUGH A NITROSOKETENE INTERMEDIATE AND THEIR USE FOR THE STEREOSELECTIVE SYNTHESIS OF AMINO-ACIDS
    KATAGIRI, N
    SATO, H
    KURIMOTO, A
    OKADA, M
    YAMADA, A
    KANEKO, C
    JOURNAL OF ORGANIC CHEMISTRY, 1994, 59 (26): : 8101 - 8106
  • [4] Synthesis of chiral spiro 3-oxazolin-5-one 3-oxides (Chiral nitrones) via a nitrosoketene intermediate and their asymmetric 1,3-dipolar cycloaddition reactions leading to the EPC synthesis of modified amino acids.
    Katagiri, N
    Okada, M
    Morishita, Y
    Kaneko, C
    TETRAHEDRON, 1997, 53 (16) : 5725 - 5746
  • [5] Synthesis of Nitrones and Nitroalkanes via Chiral Cyclic Imines
    Hu, Ying
    Zhao, Yu
    Peng, Jun-Feng
    Dong, Lin
    Xu, Yan-Jun
    ORGANIC LETTERS, 2024, 26 (22) : 4616 - 4620
  • [6] NONPROTEINOGENIC AMINO-ACIDS .4. EPC SYNTHESIS OF L-(+)-FORPHENICINE
    WEINGES, K
    REINEL, U
    MAURER, W
    GASSLER, N
    LIEBIGS ANNALEN DER CHEMIE, 1987, (10): : 833 - 838
  • [7] An efficient synthesis of chiral cyclic β-amino acids via asymmetric hydrogenation
    Pousset, C
    Callens, R
    Marinetti, A
    Larchevêque, M
    SYNLETT, 2004, (15) : 2766 - 2770
  • [8] Synthesis of nonproteinogenic amino acids by photocyclization of amidoketones
    Wessig, P
    Steiner, A
    Schwarz, J
    JOURNAL OF INFORMATION RECORDING, 1998, 24 (3-4): : 295 - 297
  • [9] Synthesis of Chiral Amino Cyclic Phosphoric Acids
    Zhang Zhan
    WuhanUniversityJournalofNaturalSciences, 2000, (04) : 497 - 499
  • [10] ENANTIOSELECTIVE SYNTHESIS OF NONPROTEINOGENIC AMINO-ACIDS
    SCHOLLKOPF, U
    TOPICS IN CURRENT CHEMISTRY, 1983, 109 : 65 - 84
12345