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

页码：1840 / 1846

页数：7

共 84 条

[1] Asymmetric Synthesis of 4-Amino-4H-Chromenes by Organocatalytic Oxa-Michael/Aza-Baylis Hillman Tandem Reactions [J].

Aleman, Jose ;

Nunez, Alberto ;

Marzo, Leyre ;

Marcos, Vanesa ;

Alvarado, Cuauhtemoc ;

Garcia Ruano, Jose Luis .

CHEMISTRY-A EUROPEAN JOURNAL, 2010, 16 (31) :9453-9456

[2] Dual catalyst control in the enantioselective intramolecular Morita-Baylis-Hillman reaction [J].

Aroyan, CE ;

Vasbinder, MM ;

Miller, SJ .

ORGANIC LETTERS, 2005, 7 (18) :3849-3851

[3] Organocatalysis - Organocatalysis lost: Modern chemistry, ancient chemistry, and an unseen biosynthetic apparatus [J].

Barbas, Carlos F., III .

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 [J].

Bennie, L ;

Malan, E ;

Coetzee, J ;

Ferreira, D .

PHYTOCHEMISTRY, 2000, 53 (07) :785-793

[6] Dienamine catalysis:: Organocatalytic asymmetric γ-amination of α,β unsaturated aldehydes [J].

Bertelsen, Slren ;

Marigo, Mauro ;

Brandes, Sebastian ;

Diner, Peter ;

Jorgensen, Karl Anker .

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 [J].

Céspedes, CL ;

Achnine, L ;

Lotina-Hennsen, B ;

Salazar, JR ;

Gómez-Garibay, F ;

Calderón, JS .

PESTICIDE BIOCHEMISTRY AND PHYSIOLOGY, 2001, 69 (02) :63-76

[8] An unexpected inversion of enantioselectivity in the proline catalyzed intramolecular Baylis-Hillman reaction [J].

Chen, SH ;

Hong, BC ;

Su, CF ;

Sarshar, S .

TETRAHEDRON LETTERS, 2005, 46 (51) :8899-8903

[9] Synthesis, structural and conformational study of chromane derivatives [J].

Ciolkowski, Michal ;

Malecka, Magdalena ;

Modranka, Roman ;

Budzisz, Elzbieta .

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 [J].

Coetzee, J ;

Malan, E ;

Ferreira, D .

TETRAHEDRON, 1998, 54 (31) :9153-9160

← 1 2 3 4 5 6 7 8 9 →