Diastereoselectivity in Diels-Alder Cycloadditions of Erythrose Benzylideneacetal 1,3-Butadienes with Maleimides

被引：4
|
作者：
Salgueiro, Daniela A. L. [1 ]
Duarte, Vera C. M. [1 ]
Sousa, Cristina E. A. [1 ]
Alves, Maria J. [1 ]
Fortes, Antonio Gil [1 ]
机构：
[1] Univ Minho, Dept Quim, P-4710057 Braga, Portugal
来源：
SYNLETT | 2012年 / 12期
关键词：
maleimides; D-erythrose benzylidene-acetal 1,3-butadiene; Diels-Alder cycloaddition; selectivity; PLANE-NONSYMMETRIC CYCLOPENTADIENES; LEWIS-ACID TEMPLATE; FACIAL SELECTIVITY; CHIRAL DIENES; COMPONENTS;
D O I：
10.1055/s-0031-1289785
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Maleimides were combined with D-erythrose benzylidene-acetal 1,3-butadienes to study the facial selectivity of the Diels-Alder cycloadditions. The selectivity was found to range from moderate to good. The reaction diastereotopicity can be reversed with the temperature. Simultaneous coordination of the diene, having a free hydroxy group, and maleimide to a chiral bimetallic Lewis acid catalyst (LACASA-DA reaction) occurs with complete diastereocontrol to give a single adduct, using an extra chiral inductor either (R)- or (S)-BINOL.
引用
收藏
页码：1765 / 1768
页数：4
相关论文
共 50 条
  • [31] High-Pressure Diels-Alder Cycloadditions between Benzylideneacetones and 1,3-Butadienes: Application to the Synthesis of (R,R)-(-)- and (S,S)-(+)-Δ8-Tetrahydrocannabinol
    Ballerini, Eleonora
    Minuti, Lucio
    Piermatti, Oriana
    JOURNAL OF ORGANIC CHEMISTRY, 2010, 75 (12): : 4251 - 4260
  • [32] Diastereo-controlled Diels-Alder cycloadditions of erythrose benzylidene-acetal 1,3-butadienes by 4-substituted-1,2,4-triazoline-3,5-dione: Evidence for the stereoelectronic effects on the dienes
    Alves, Maria J.
    Duarte, Vera C. M.
    Faustino, Helio
    Fortes, Antonio Gil
    TETRAHEDRON-ASYMMETRY, 2010, 21 (15) : 1817 - 1820
  • [33] ABINITIO INVESTIGATION OF DIELS-ALDER REACTIONS OF MONO-PHOSPHA AND AZA-1,3-BUTADIENES WITH ETHYLENE
    LIU, MX
    BACHRACH, SM
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 1992, 203 : 229 - ORGN
  • [34] Diastereoselective Diels-Alder reactions of N-sulfonyl-1-aza-1,3-butadienes with optically active enol ethers: An asymmetric variant of the 1-azadiene Diels-Alder reaction
    Clark, Ryan C.
    Pfeiffer, Steven S.
    Boger, Dale L.
    Journal of the American Chemical Society, 2006, 128 (08): : 2587 - 2593
  • [35] REARRANGEMENT REACTIONS .3. SYNTHESES AND DIELS-ALDER REACTIONS OF 2-ALKYLAZO-SUBSTITUTED 1,3-BUTADIENES
    BANERT, K
    HAGEDORN, M
    TETRAHEDRON LETTERS, 1992, 33 (48) : 7331 - 7334
  • [36] Intermolecular Diels-Alder Cycloaddition/Cross-Coupling Sequences of 2-Bromo-1,3-butadienes
    Choi, Hans
    Shirley, Harry J.
    Aitken, Harry R. M.
    Schulte, Tim
    Sohnel, Tilo
    Hume, Paul A.
    Brimble, Margaret A.
    Furkert, Daniel P.
    ORGANIC LETTERS, 2020, 22 (03) : 1022 - 1027
  • [37] DIASTEREOFACIAL SELECTIVITY IN DIELS-ALDER REACTIONS OF CHIRAL 1,2-DIAZA-1,3-BUTADIENES DERIVED FROM CARBOHYDRATES
    AVALOS, M
    BABIANO, R
    CINTAS, P
    JIMENEZ, JL
    MOLINA, MM
    PALACIOS, JC
    SANCHEZ, JB
    TETRAHEDRON LETTERS, 1991, 32 (22) : 2513 - 2516
  • [38] Hetero Diels-Alder reactions of 1-amino-3-siloxy-1,3-butadienes under strictly thermal conditions
    Huang, Y
    Rawal, VH
    ORGANIC LETTERS, 2000, 2 (21) : 3321 - 3323
  • [39] CHIRAL 2-ALKOXY-1,3-BUTADIENES - SYNTHESIS AND FACE-SELECTIVITY IN DIELS-ALDER REACTIONS
    BARLUENGA, J
    TOMAS, M
    SUAREZSOBRINO, A
    LOPEZ, LA
    JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1995, (17) : 1785 - 1786
  • [40] SPONTANEOUS HOMOPOLYMERIZATION COMPETES WITH DIELS-ALDER CYCLOADDITION OF 1-ARYL-1,3-BUTADIENES TO DIENOPHILES CONTAINING A LEAVING GROUP
    CLEVER, HA
    WANG, GY
    MOLLBERG, WC
    PADIAS, AB
    HALL, HK
    JOURNAL OF ORGANIC CHEMISTRY, 1992, 57 (25): : 6837 - 6842
12345