Synthesis of 4-Hydroxy-4H-chromenes by Reaction of Salicylic Aldehydes with Alkynals Catalyzed by Silyl Prolinol Ethers

被引：21
作者：
Aleman, Jose [1 ]
Alvarado, Cuauhtemoc [1 ]
Marcos, Vanesa [1 ]
Nunez, Alberto [1 ]
Garcia Ruano, Jose Luis [1 ]
机构：
[1] Univ Autonoma Madrid, Dept Quim Organ CI, E-28049 Madrid, Spain
来源：
SYNTHESIS-STUTTGART | 2011年 / 12期
关键词：
organocatalysis; proline; chromenes; asymmetric synthesis; aminocatalysis; BAYLIS-HILLMAN REACTION; ONE-POT ACCESS; ASYMMETRIC-SYNTHESIS; ALPHA; BETA-UNSATURATED ALDEHYDES; PART; FUNCTIONALIZATION; ORGANOCATALYSIS; FLAVONOIDS; 4H-CHROMENES; DERIVATIVES;
D O I：
10.1055/s-0030-1260020
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
We report an oxa-Michael/Baylis-Hillman tandem reaction between salicylaldehydes and alk-2-ynals activated by silyl prolinol ethers, affording 2,3-disubstituted 4-hydroxy-4H-chromenes in good yields and enantiomeric ratios (up to 98:2).
引用
收藏
页码：1840 / 1846
页数：7
相关论文
共 84 条
  • [1] Asymmetric Synthesis of 4-Amino-4H-Chromenes by Organocatalytic Oxa-Michael/Aza-Baylis Hillman Tandem Reactions
    Aleman, Jose
    Nunez, Alberto
    Marzo, Leyre
    Marcos, Vanesa
    Alvarado, Cuauhtemoc
    Garcia Ruano, Jose Luis
    [J]. CHEMISTRY-A EUROPEAN JOURNAL, 2010, 16 (31) : 9453 - 9456
  • [2] Dual catalyst control in the enantioselective intramolecular Morita-Baylis-Hillman reaction
    Aroyan, CE
    Vasbinder, MM
    Miller, SJ
    [J]. ORGANIC LETTERS, 2005, 7 (18) : 3849 - 3851
  • [3] Organocatalysis - Organocatalysis lost: Modern chemistry, ancient chemistry, and an unseen biosynthetic apparatus
    Barbas, Carlos F., III
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2008, 47 (01) : 42 - 47
  • [4] BATT DG, 2010, Patent No. 2010009069
  • [5] Oligomeric flavonoids -: Part 32 -: Structure and synthesis of ether-linked proteracacinidin and promelacacinidin proanthocyanidins from Acacia caffra
    Bennie, L
    Malan, E
    Coetzee, J
    Ferreira, D
    [J]. PHYTOCHEMISTRY, 2000, 53 (07) : 785 - 793
  • [6] Dienamine catalysis:: Organocatalytic asymmetric γ-amination of α,β unsaturated aldehydes
    Bertelsen, Slren
    Marigo, Mauro
    Brandes, Sebastian
    Diner, Peter
    Jorgensen, Karl Anker
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (39) : 12973 - 12980
  • [7] Inhibition of photophosphorylation and electron transport by flavonoids and biflavonoids from endemic Tephrosia spp. of Mexico
    Céspedes, CL
    Achnine, L
    Lotina-Hennsen, B
    Salazar, JR
    Gómez-Garibay, F
    Calderón, JS
    [J]. PESTICIDE BIOCHEMISTRY AND PHYSIOLOGY, 2001, 69 (02) : 63 - 76
  • [8] An unexpected inversion of enantioselectivity in the proline catalyzed intramolecular Baylis-Hillman reaction
    Chen, SH
    Hong, BC
    Su, CF
    Sarshar, S
    [J]. TETRAHEDRON LETTERS, 2005, 46 (51) : 8899 - 8903
  • [9] Synthesis, structural and conformational study of chromane derivatives
    Ciolkowski, Michal
    Malecka, Magdalena
    Modranka, Roman
    Budzisz, Elzbieta
    [J]. JOURNAL OF MOLECULAR STRUCTURE, 2009, 937 (1-3) : 139 - 145
  • [10] Oligomeric flavanoids - Part 29: Structure and synthesis of novel ether-linked [4-O-4]bis-teracacinidins
    Coetzee, J
    Malan, E
    Ferreira, D
    [J]. TETRAHEDRON, 1998, 54 (31) : 9153 - 9160
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