Metal-Free Bronsted Acid Catalyzed Formal [3+3] Annulation. Straightforward Synthesis of Dihydro-2H-Chromenones, Pyranones, and Tetrahydroquinolinones

被引：69

作者：

Moreau, Julie ^{[3
]}

Hubert, Claudie ^{[3
]}

Batany, Jessika ^{[3
]}

Toupet, Loic ^{[2
]}

Roisnel, Thierry ^{[3
]}

Hurvois, Jean-Pierre ^{[3
]}

Renaud, Jean-Luc ^{[1
]}

机构：

[1] Univ Caen, Lab Chim Mol & Thioorgan, INC3M, ENSICAEN,FR 3038,UMR 6507, F-14050 Caen, France

[2] Univ Rennes 1, Inst Phys, Grp Mat Condensee & Mat, CNRS,UMR 6626, F-35042 Rennes, France

[3] Univ Rennes 1, CNRS, UMR 6226, F-35042 Rennes, France

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2009年 / 74卷 / 23期

关键词：

SELECTIVE ACETYLCHOLINESTERASE INHIBITORS; PYRANOCHALCONE NATURAL-PRODUCTS; CONCISE TOTAL-SYNTHESIS; PENICILLIUM SP FO-4259; ALPHA; BETA-UNSATURATED ALDEHYDES; EFFICIENT SYNTHESIS; BIOMIMETIC SYNTHESIS; ARISUGACIN-A; DERIVATIVES; ORGANOCATALYSIS;

D O I：

10.1021/jo901238y

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Bronsted acids catalyze the addition of enolizable beta-diketones, beta-ketoesters, and vinylogous amides to alpha,beta-unsaturated aldehydes to lead to substituted chromenones, pyranones, and tetrahydroquinolinones in good yields under mild reaction conditions via a formal [3 + 3] cycloaddition.

引用

页码：8963 / 8973

页数：11

共 74 条

[1] Stronger bronsted acids [J].

Akiyama, Takahiko .

CHEMICAL REVIEWS, 2007, 107 (12) :5744-5758

[2] Recent progress in chiral Bronsted acid catalysis [J].

Akiyama, Takahiko ;

Itoh, Junji ;

Fuchibe, Kohei .

ADVANCED SYNTHESIS & CATALYSIS, 2006, 348 (09) :999-1010

[3] A straightforward entry into polyketide monoprenylated furanocoumarins and pyranocoumarins [J].

Appendino, G ;

Cravotto, G ;

Giovenzana, GB ;

Palmisano, G .

JOURNAL OF NATURAL PRODUCTS, 1999, 62 (12) :1627-1631

[4]

BHAT SV, 1977, TETRAHEDRON LETT, P1669, DOI 10.1016/S0040-4039(01)93245-9

[5] REACTIONS OF FORSKOLIN, A BIOLOGICALLY-ACTIVE DITERPENOID FROM COLEUS-FORSKOHLII [J].

BHAT, SV ;

BAJWA, BS ;

DORNAUER, H ;

DESOUZA, NJ .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1982, (03) :767-771

[6] Protonated chiral catalysts: Versatile tools for asymmetric synthesis [J].

Bolm, C ;

Rantanen, T ;

Schiffers, I ;

Zani, L .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2005, 44 (12) :1758-1763

[7] Unique structural topology and reactivities of the ABD tricycle in phomactin A [J].

Cole, KP ;

Hsung, RP .

CHEMICAL COMMUNICATIONS, 2005, (46) :5784-5786

[8] Organocatalysis mediated by (thio)urea derivatives [J].

Connon, Stephen J. .

CHEMISTRY-A EUROPEAN JOURNAL, 2006, 12 (21) :5418-5427

[9]

Cravotto G, 2001, SYNTHESIS-STUTTGART, P49

[10] Organocatalytic synthesis of drugs and bioactive natural products [J].

de Figueiredo, Renata Marcia ;

Christmann, Mathias .

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2007, 2007 (16) :2575-2600

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