PPh3-Catalyzed Domino Reaction: A Facile Method for the Synthesis of Chroman Derivatives

被引：112

作者：

Meng, Xiangtai

Huang, You ^{[1
]}

Zhao, Hongxia

Xie, Peizhong

Ma, Jianze

Chen, Ruyu

机构：

[1] Nankai Univ, State Key Lab, Tianjin 300071, Peoples R China

来源：

ORGANIC LETTERS | 2009年 / 11卷 / 04期

基金：

中国国家自然科学基金;

关键词：

CATALYZED 3+2 CYCLOADDITION; ELECTRON-DEFICIENT OLEFINS; ASSISTED PHOSPHINE CATALYSIS; COMBINATORIAL LIBRARIES; PRIVILEGED STRUCTURES; 4+2 ANNULATION; SALICYLIC ALDEHYDES; ALLENIC KETONES; IMINES; 2,3-BUTADIENOATES;

D O I：

10.1021/ol802917d

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A novel domino reaction catalyzed by triphenylphosphine was developed for synthesis of the highly functionalized chroman derivatives. The first example that the gamma-CH3 of allenoate undergoes cyclization to form chroman derivates was reported.

引用

收藏

页码：991 / 994

页数：4

相关论文

共 67 条

[1]

ARNAUD V, 2008, J AM CHEM SOC, V130, P14030

[2] DISCOVERY OF INSECT ANTI-JUVENILE HORMONES IN PLANTS [J].

BOWERS, WS ;

OHTA, T ;

CLEERE, JS ;

MARSELLA, PA .

SCIENCE, 1976, 193 (4253) :542-547

[3] Small-molecule inhibitors of protein geranylgeranyltransferase type I [J].

Castellano, Sabrina ;

Fiji, Hannah D. G. ;

Kinderman, Sape S. ;

Watanabe, Masaru ;

de Leon, Pablo ;

Tamanoi, Fuyuhiko ;

Kwon, Ohyun .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2007, 129 (18) :5843-+

[4] A highly efficient and practical synthesis of chromene derivatives using ring-closing olefin metathesis [J].

Chang, SB ;

Grubbs, RH .

JOURNAL OF ORGANIC CHEMISTRY, 1998, 63 (03) :864-866

[5] Enantioselective [3+2]-cycloadditions catalyzed by a protected, multifunctional phosphine-containing α-amino acid [J].

Cowen, Bryan J. ;

Miller, Scott J. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2007, 129 (36) :10988-+

[6] Theory-guided design of Bronsted acid-assisted phosphine catalysis: synthesis of dihydropyrones from aldehydes and allenoates [J].

Creech, Gardner S. ;

Zhu, Xue-Feng ;

Foncivic, Branden ;

Dudding, Travis ;

Kwon, Ohyun .

TETRAHEDRON, 2008, 64 (29) :6935-6942

[7] Alcohol-assisted phosphine catalysis: One-step syntheses of dihydropyrones from aldehydes and allenoates [J].

Creech, Gardner S. ;

Kwon, Ohyun .

ORGANIC LETTERS, 2008, 10 (03) :429-432

[8] A facile synthetic route to 2H-chromenes:: Reconsideration of the mechanism of the DBU-catalyzed reaction between salicylic aldehydes and ethyl 2-methylbuta-2,3-dienoate [J].

Dai, Lun-Zhi ;

Shi, Yong-Ling ;

Zhao, Gui-Ling ;

Shi, Min .

CHEMISTRY-A EUROPEAN JOURNAL, 2007, 13 (13) :3701-3706

[9] VAPOR-PHASE INTRODUCTION OF VINYL KETONES IN MICHAEL ADDITIONS [J].

DEBOER, CD .

JOURNAL OF ORGANIC CHEMISTRY, 1974, 39 (16) :2426-2427

[10] A phosphine-catalyzed [3+2] cycloaddition strategy leading to the first total synthesis of (-)-hinesol [J].

Du, YS ;

Lu, XY .

JOURNAL OF ORGANIC CHEMISTRY, 2003, 68 (16) :6463-6465

← 1 2 3 4 5 6 7 →