Copper(II)-Bis(oxazoline) catalyzed asymmetric Diels-Alder reaction with α'-arylsulfonyl enones as dienophiles

被引:16
|
作者
Barroso, Santiago [2 ]
Blay, Gonzalo [2 ]
Al-Midfa, Lina [2 ]
Munoz, M. Carmen [1 ]
Pedro, Jose R. [2 ]
机构
[1] Univ Politecn Valencia, Dept Fis Aplicada, E-46071 Valencia, Spain
[2] Univ Valencia, Dept Quim Organ, Fac Quim, E-46100 Burjassot, Valencia, Spain
来源
JOURNAL OF ORGANIC CHEMISTRY | 2008年 / 73卷 / 16期
关键词
D O I
10.1021/jo8009227
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
[GRAPHICS] alpha'-Arylsulfonyl enones are efficient bidentate dienophiles for the Cu(II)-bis(oxazoline) catalyzed enantioselective Diels-Alder reaction with a number of dienes, affording the corresponding products with good to high enantiomeric excesses. The resulting products can be alkylated and the sulfone removed, so alpha'-arylsulfonyl enones can be regarded as surrogates of simple monodentate enones, which are poor dienophiles with this catalytic system.
引用
收藏
页码:6389 / 6392
页数:4
相关论文
共 50 条
  • [21] A molecular mechanics study of copper(II)-catalyzed asymmetric Diels-Alder reactions
    Deeth, RJ
    Fey, N
    ORGANOMETALLICS, 2004, 23 (05) : 1042 - 1054
  • [22] Ionic Liquid Effect on the Reversal of Configuration for the Magnesium(II) and Copper(II) Bis(oxazoline)-Catalysed Enantioselective Diels-Alder Reaction
    Goodrich, P.
    Hardacre, C.
    Paun, C.
    Parvulescu, V. I.
    Podolean, I.
    ADVANCED SYNTHESIS & CATALYSIS, 2008, 350 (16) : 2473 - 2476
  • [23] Dihydropyrones as dienophiles in the Diels-Alder reaction.
    Chen, DQ
    Totah, NI
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 1997, 213 : 173 - ORGN
  • [24] Cationic copper(II)-oxazoline-sulfoxide catalysts: Application to asymmetric Diels-Alder reactions
    Watanabe, K
    Hirasawa, T
    Hiroi, K
    HETEROCYCLES, 2002, 58 : 93 - 97
  • [25] ASYMMETRIC DIELS-ALDER REACTION CATALYZED BY CHIRAL BASES
    RIANT, O
    KAGAN, HB
    TETRAHEDRON LETTERS, 1989, 30 (52) : 7403 - 7406
  • [26] THE DIELS-ALDER REACTION ETHYLENIC AND ACETYLENIC DIENOPHILES
    HOLMES, HL
    ORGANIC REACTIONS, 1947, 4 : 60 - 173
  • [27] DIELS-ALDER REACTION OF FURAN WITH SOME DIENOPHILES
    EGGELTE, TA
    KONING, HD
    HUISMAN, HO
    TETRAHEDRON, 1973, 29 (16) : 2491 - 2493
  • [28] Masked Ketenes as Dienophiles in the Diels-Alder Reaction
    Mackay, Emily G.
    Newton, Christopher G.
    AUSTRALIAN JOURNAL OF CHEMISTRY, 2016, 69 (12) : 1365 - 1374
  • [29] Diels-Alder reaction of heterocyclic imine dienophiles
    Hedberg, C
    Pinho, P
    Roth, P
    Andersson, PG
    JOURNAL OF ORGANIC CHEMISTRY, 2000, 65 (09): : 2810 - 2812
  • [30] ASYMMETRIC DIELS-ALDER CYCLOADDITIONS WITH CHIRAL CARBAMOYL DIENOPHILES
    DEFOIN, A
    BROUILLARDPOICHET, A
    STREITH, J
    HELVETICA CHIMICA ACTA, 1992, 75 (01) : 109 - 123