Asymmetric base-catalyzed Diels-Alder reaction of 3-hydroxy-2-pyrone with chiral acrylate derivatives

被引:36
|
作者
Okamura, H [1 ]
Morishige, K [1 ]
Iwagawa, T [1 ]
Nakatani, M [1 ]
机构
[1] Kagoshima Univ, Fac Sci, Dept Chem, Kagoshima 890, Japan
关键词
D O I
10.1016/S0040-4039(97)10843-7
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
In the presence of a cinchona alkaloid as a catalyst, the Diels-Alder reaction of 3-hydroxy-2-pyrone with chiral N-acryloyl oxazolidinone afforded a bicyclolactone adduct with high diastereoselectivities (up to 95%de) in almost quantitative yield. (C) 1998 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:1211 / 1214
页数:4
相关论文
共 50 条
  • [31] ASYMMETRIC DIELS-ALDER REACTION - DESIGN OF CHIRAL DIENOPHILES
    CHOY, W
    REED, LA
    MASAMUNE, S
    JOURNAL OF ORGANIC CHEMISTRY, 1983, 48 (07): : 1137 - 1139
  • [32] Asymmetric synthesis of the key intermediate of an SP antagonist RPR107880 using a base-catalyzed Diels-Alder reaction
    Okamura, H
    Shimizu, H
    Nakamura, Y
    Iwagawa, T
    Nakatani, M
    TETRAHEDRON LETTERS, 2000, 41 (21) : 4147 - 4150
  • [33] STUDY ON THE REACTION-MECHANISM OF THE BASE-CATALYZED INTRAMOLECULAR DIELS-ALDER REACTION OF FURFURYL PROPARGYL ETHERS
    WU, HJ
    YING, FH
    SHAO, WD
    JOURNAL OF ORGANIC CHEMISTRY, 1995, 60 (19): : 6168 - 6172
  • [34] A Lewis base-catalyzed hetero Diels-Alder reaction between aldehydes and the Danishefsky's diene
    Mukaiyama, T
    Kitazawa, T
    Fujisawa, H
    CHEMISTRY LETTERS, 2006, 35 (03) : 328 - 329
  • [35] Use of 9-anthrylcarbinol derivatives as chiral auxiliaries in asymmetric Diels-Alder reaction
    Carriere, A
    Virgili, A
    TETRAHEDRON-ASYMMETRY, 1996, 7 (01) : 227 - 230
  • [36] A New Chiral β-Sulfiny Dienophile for Asymmetric Diels-Alder Reaction
    YANG TengKuei
    HUNG ShunMing
    CHEN ChinZon
    JIANG YaoZhong
    MI AiQiao Department of Chemistry National ChungHsing University Taichung Taiwan Chengdu Institute of Organic Chemistry Academia Sinica Chengdu
    有机化学, 1993, (02) : 183 - 185
  • [37] Asymmetric Diels-Alder Reaction Involving Chiral Benzimidazoles as Organocatalysts
    Mirgane, Nitin A.
    Karnik, Anil V.
    CHIRALITY, 2011, 23 (05) : 404 - 407
  • [38] ASYMMETRIC DIELS-ALDER REACTION PROMOTED BY A CHIRAL TITANIUM REAGENT
    NARASAKA, K
    INOUE, M
    OKADA, N
    CHEMISTRY LETTERS, 1986, (07) : 1109 - 1112
  • [39] Chiral phosphinooxathiane ligands for catalytic asymmetric Diels-Alder reaction
    Nakano, H
    Suzuki, Y
    Kabuto, C
    Fujita, R
    Hongo, H
    JOURNAL OF ORGANIC CHEMISTRY, 2002, 67 (14): : 5011 - 5014
  • [40] Exo-selective asymmetric Diels-Alder reaction of acrylate ester
    Kawamura, M
    Kudo, K
    CHIRALITY, 2002, 14 (09) : 727 - 730