Lewis acid-promoted synthesis and reactivity of β-O-benzylhydroxylamino imides derived from D-glyceraldehyde

被引:20
作者
Cardillo, G [1 ]
Gentilucci, L [1 ]
De Matteis, V [1 ]
机构
[1] Univ Bologna, Dipartimento Chim G Ciamician, I-40128 Bologna, Italy
关键词
D O I
10.1021/jo0259055
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
This paper describes the synthesis and use of beta-hydroxylamino imides derived from D-glyceraldehyde possessing a number of reactive sites that operate synergistically or alternatively to bring about highly regio- and diastereoselective transformations to give an optically pure aziridine-2-imide, a dihydro pyrimidine-2,4-dione, or a lactone. Both the syntheses, via the diastereoselective 1,4-conjugate addition of O-benzyl hydroxylamine to alpha,beta-unsaturated imides, and transformations can be simply tuned by choosing between different Lewis acids.
引用
收藏
页码:5957 / 5962
页数:6
相关论文
共 46 条
  • [1] HYDROGENATION OF 1-BENZYL-3-(2,2-DIMETHYL-1,3-DIOXOLAN-4-YL)-AZIRIDINE-2-CARBOXYLIC ACID ETHYL-ESTER
    AMBROSI, HD
    DUCZEK, W
    RAMM, M
    JAHNISCH, K
    [J]. TETRAHEDRON LETTERS, 1994, 35 (41) : 7613 - 7616
  • [2] AMBROSI HD, 1994, LIEBIGS ANN CHEM, P1013
  • [3] LEWIS ACID-PROMOTED 1,4-ADDITION TO CHIRAL IMIDE DERIVATIVES IN THE SYNTHESIS OF BETA-AMINO ACIDS
    AMOROSO, R
    CARDILLO, G
    SABATINO, P
    TOMASINI, C
    TRERE, A
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1993, 58 (21) : 5615 - 5619
  • [4] Conjugate addition of amines to α,β-enones promoted by CeCl3•7H2O-NaI system supported in silica gel
    Bartoli, G
    Bosco, M
    Marcantoni, E
    Petrini, M
    Sambri, L
    Torregiani, E
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2001, 66 (26) : 9052 - 9055
  • [5] ALPHA-AMINO OR BETA-AMINO POLYHYDROXY ACIDS FROM THE REACTION OF BROMODEOXYALDONOLACTONES WITH LIQUID-AMMONIA
    BOLS, M
    LUNDT, I
    [J]. ACTA CHEMICA SCANDINAVICA, 1991, 45 (03): : 280 - 284
  • [6] Synthesis of enantiomerically pure aziridine-2-imides by cyclization of chiral 3′-benzyloxyamino imide enolates
    Bongini, A
    Cardillo, G
    Gentilucci, L
    Tomasini, C
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1997, 62 (26) : 9148 - 9153
  • [7] Conjugate addition of hydroxylamino derivatives to alkylidene malonates in the presence of chiral Lewis acids
    Cardillo, G
    Gentilucci, L
    Gianotti, M
    Kim, H
    Perciaccante, R
    Tolomelli, A
    [J]. TETRAHEDRON-ASYMMETRY, 2001, 12 (17) : 2395 - 2398
  • [8] Synthesis of aziridine-2,2-dicarboxylates via 1,4-addition of N,O-(bistrimethylsilyl)hydroxylamine to α,β-unsaturated malonates
    Cardillo, G
    Gentilucci, L
    Gianotti, M
    Perciaccante, R
    Tolomelli, A
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2001, 66 (25) : 8657 - 8660
  • [9] NMR investigations on boron complexes in the conjugate addition on α,β-unsaturated imides
    Cardillo, G
    Gentilucci, L
    Gianotti, M
    Tolomelli, A
    [J]. ORGANIC LETTERS, 2001, 3 (08) : 1165 - 1167
  • [10] Asymmetric synthesis of alkyl aziridine-2-carboxylates from chiral 3'-benzyloxy-aminoimides
    Cardillo, G
    Casolari, S
    Gentilucci, L
    Tomasini, C
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1996, 35 (16): : 1848 - 1849