Catalytic asymmetric Diels-Alder reactions of α-thioacrylates for the preparation of norbornenone

被引：31
|
作者：
Aggarwal, VK [1 ]
Anderson, ES
Jones, DE
Obierey, KB
Giles, R
机构：
[1] Univ Sheffield, Dept Chem, Sheffield S3 7HF, S Yorkshire, England
[2] SmithKline Beecham, Tonbridge TN11 9AN, Kent, England
来源：
CHEMICAL COMMUNICATIONS | 1998年 / 18期
关键词：
D O I：
10.1039/a805366i
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
Cu-II-bisoxazoline complexes catalyse the asymmetric Diels-Alder cycloaddition of alpha-thioacrylates with cyclopentadiene to give the cycloadducts in up to 92% yield, 88% de and >95% ee for the endo product; deprotection gives good yields of (1S,4S)-norbornenone with high enantioselectivity.
引用
收藏
页码：1985 / 1986
页数：2
相关论文
共 50 条
  • [1] CATALYTIC ASYMMETRIC DIELS-ALDER REACTIONS
    KAGAN, HB
    RIANT, O
    CHEMICAL REVIEWS, 1992, 92 (05) : 1007 - 1019
  • [2] Copper(II)-bisoxazoline-catalysed asymmetric Diels-Alder reactions of α-thioacrylates
    Aggarwal, VK
    Jones, DE
    Martin-Castro, AM
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2000, 2000 (16) : 2939 - 2945
  • [3] INTERMOLECULAR ASYMMETRIC DIELS-ALDER REACTIONS
    MORI, Y
    JOURNAL OF SYNTHETIC ORGANIC CHEMISTRY JAPAN, 1982, 40 (04) : 321 - 331
  • [4] CATALYTIC ASYMMETRIC DIELS-ALDER REACTIONS OF 2-PYRONE DERIVATIVES
    MARKO, IE
    EVANS, GR
    DECLERCQ, JP
    TETRAHEDRON, 1994, 50 (15) : 4557 - 4574
  • [5] Catalytic asymmetric Diels-Alder reactions involving aryl vinyl ketones
    Kong, Liman
    Han, Xiaoyu
    Jiao, Peng
    CHEMICAL COMMUNICATIONS, 2014, 50 (91) : 14113 - 14116
  • [6] Progress of Catalytic Asymmetric Diels-Alder Reactions of 2-Pyrones
    Xu Mengmeng
    Cai Quan
    CHINESE JOURNAL OF ORGANIC CHEMISTRY, 2022, 42 (03) : 698 - 713
  • [7] VAULTED BIARYLS AS CHIRAL LIGANDS FOR ASYMMETRIC CATALYTIC DIELS-ALDER REACTIONS
    BAO, JM
    WULFF, WD
    RHEINGOLD, AL
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1993, 115 (09) : 3814 - 3815
  • [8] New approaches to catalytic asymmetric nitroso diels-alder reactions.
    Whiting, A
    Wan, H
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2002, 224 : U213 - U213
  • [9] HETEROGENEOUS CATALYSIS OF ASYMMETRIC DIELS-ALDER REACTIONS
    CATIVIELA, C
    FRAILE, JM
    GARCIA, JI
    MAYORAL, JA
    PIRES, E
    FIGUERAS, F
    JOURNAL OF MOLECULAR CATALYSIS, 1994, 89 (1-2): : 159 - 164
  • [10] Asymmetric Diels-Alder reactions in ionic liquids
    Meracz, I
    Oh, T
    TETRAHEDRON LETTERS, 2003, 44 (34) : 6465 - 6468
12345