Synthesis of enantiopure 3-hydroxymethylchromanes via intramolecular nitrone cycloaddition

被引:34
|
作者
Broggini, G
Folcio, F
Sardone, N
Sonzogni, M
Zecchi, G
机构
[1] UNIV MILAN,DIPARTIMENTO CHIM ORGAN & IND,I-20133 MILAN,ITALY
[2] UNIV PAVIA,CTR GRANDI STRUMENTI,I-27100 PAVIA,ITALY
关键词
D O I
10.1016/0957-4166(96)00076-6
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
Enantiopure (R) and (S) 3-hydroxymethylchromanes were prepared by the intramolecular nitrone cycloaddition strategy, starting from allyl-type ethers of 2-hydroxybenzaldehydes and using (R)-N-(alpha-phenylethyl)hydroxylamine as chiral auxiliary.
引用
收藏
页码:797 / 806
页数:10
相关论文
共 50 条
  • [1] Synthesis of enantiopure 4-amino-3-hydroxymethyl-tetrahydroquinolines via an intramolecular nitrone cycloaddition
    Broggini, Gianluigi
    Colombo, Francesco
    De Marchi, Ivan
    Galli, Simona
    Martinelli, Michela
    Zecchi, Gaetano
    TETRAHEDRON-ASYMMETRY, 2007, 18 (12) : 1495 - 1501
  • [2] STEREOSPECIFIC CYCLOPENTANE SYNTHESIS VIA INTRAMOLECULAR NITRONE CYCLOADDITION
    VINICK, FJ
    FENGLER, IE
    GSCHWEND, HW
    RODEBAUGH, RK
    JOURNAL OF ORGANIC CHEMISTRY, 1977, 42 (17): : 2936 - 2937
  • [3] FACILE BRIDGED BICYCLOALKANE SYNTHESIS VIA INTRAMOLECULAR NITRONE OLEFIN CYCLOADDITION
    FUNK, RL
    HORCHER, LHM
    DAGGETT, JU
    HANSEN, MM
    JOURNAL OF ORGANIC CHEMISTRY, 1983, 48 (15): : 2632 - 2634
  • [4] Total Synthesis of (±)-Thebainone A by Intramolecular Nitrone Cycloaddition
    Wang, Yuzhou
    Hennig, Andre
    Kuettler, Thomas
    Hahn, Christian
    Jaeger, Anne
    Metz, Peter
    ORGANIC LETTERS, 2020, 22 (08) : 3145 - 3148
  • [5] Synthesis of enantiopure 4-amino-6-fluoro-3-(hydroxymethyl)chromanes via intramolecular nitrone cycloadditions
    Broggini, G
    Bruche, L
    Cappelletti, E
    Zecchi, G
    JOURNAL OF CHEMICAL RESEARCH, 1997, (02) : 36 - +
  • [6] Intramolecular nitrone cycloaddition: Stereoselective synthesis of piperidine systems
    Chiacchio, U
    Rescifina, A
    Casuscelli, F
    Piperno, A
    Pisani, V
    Romeo, R
    TETRAHEDRON, 1996, 52 (45) : 14311 - 14322
  • [7] EXPEDITIOUS SYNTHESIS OF AMINOCYCLOPENTITOLS FROM D-RIBOSE VIA INTRAMOLECULAR NITRONE CYCLOADDITION
    GALLOS, JK
    GOGA, EG
    KOUMBIS, AE
    JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1994, (06): : 613 - 614
  • [8] Asymmetric synthesis of epicylindrospermopsin via intramolecular nitrone cycloaddition. Assignment of absolute configuration
    White, JD
    Hansen, JD
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (18) : 4950 - 4951
  • [9] Rapid entry to enantiopure polycyclic β-lactams via intramolecular nitrone-alkene cycloaddition of 2-azetidinone-tethered alkenylaldehydes
    Alcaide, B
    Alonso, JM
    Aly, MF
    Sáez, E
    Martínez-Alcázar, MP
    Hernández-Cano, F
    TETRAHEDRON LETTERS, 1999, 40 (29) : 5391 - 5394
  • [10] Synthesis of enantiopure pyrrolo[3,4-c]pyrazole derivatives via intramolecular cycloaddition of homochiral nitrilimines
    Broggini, G
    Molteni, G
    Pilati, T
    Zecchi, G
    SYNTHETIC COMMUNICATIONS, 2001, 31 (24) : 3799 - 3806