Multistep One-Pot, Wittig/Nazarov Reaction for Construction of Cyclopentenone with Diazo Compounds and Acid Chlorides

被引：31

作者：

Cao, Peng ^{[1
]}

Sun, Xiu-Li ^{[1
]}

Zhu, Ben-Hu ^{[2
]}

Shen, Qi ^{[2
]}

Xie, Zuowei ^{[3
]}

Tang, Yong ^{[1
]}

机构：

[1] Chinese Acad Sci, Shanghai Inst Organ Chem, State Key Lab Organometall Chem, Shanghai 200032, Peoples R China

[2] Suzhou Univ, Sch Chem & Chem Engn, Suzhou 215123, Peoples R China

[3] Chinese Univ Hong Kong, Dept Chem, Shatin, Hong Kong, Peoples R China

来源：

ORGANIC LETTERS | 2009年 / 11卷 / 14期

基金：

中国国家自然科学基金;

关键词：

ETHER NAZAROV CYCLIZATION; CROSS-COUPLING REACTION; DOMINO REACTIONS; CHIRAL AUXILIARIES; CASCADE REACTIONS; ASYMMETRIC CYCLOPENTANNELATION; CATIONIC CYCLOPENTANNELATION; ENANTIOSELECTIVE SYNTHESIS; RING-CLOSURE; ALLENES;

D O I：

10.1021/ol901086f

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A facile multistep one-pot synthesis of single or fused cyclopentenones has been developed. The sequence involves a transition metal-catalyzed ylide formation/Wittig Olefination/Nazarov Cyclization.

引用

页码：3048 / 3051

页数：4

共 60 条

[1]

Alexander S.D., 2008, J AM CHEM SOC, V130, P1440

[2] Traceless Chiral Auxiliaries for the Allene Ether Nazarov Cyclization [J].

Banaag, April R. ;

Tius, Marcus A. .

JOURNAL OF ORGANIC CHEMISTRY, 2008, 73 (21) :8133-8141

[3] Design of chiral auxiliaries for the allene ether Nazarov cyclization [J].

Banaag, April R. ;

Tius, Marcus A. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2007, 129 (17) :5328-+

[4] Ph3As-catalyzed Wittig-type olefination of aldehydes with diazoacetate in the presence of Na2S2O4 [J].

Cao, Peng ;

Li, Chuan-Ying ;

Kang, Yan-Biao ;

Xie, Zuowei ;

Sun, Xiu-Li ;

Tang, Yong .

JOURNAL OF ORGANIC CHEMISTRY, 2007, 72 (17) :6628-6630

[5] Tandem and domino catalytic strategies for enantioselective synthesis [J].

Chapman, Christopher J. ;

Frost, Christopher G. .

SYNTHESIS-STUTTGART, 2007, (01) :1-21

[6] Gold-catalyzed cycloisomerization of 1,5-allenynes via dual activation of an ene reaction [J].

Cheong, Paul Ha-Yeon ;

Morganelli, Philip ;

Luzung, Michael R. ;

Houk, K. N. ;

Toste, F. Dean .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2008, 130 (13) :4517-4526

[7] 1,2-alkyl migration as a key element in the invention of cascade reactions catalyzed by π-acids [J].

Crone, Benedikt ;

Kirsch, Stefan F. .

CHEMISTRY-A EUROPEAN JOURNAL, 2008, 14 (12) :3514-3522

[8] The virtue of palladium-catalyzed domino reactions -: Diverse oligocyclizations of acyclic 2-bromoenynes and 2-bromoenediynes [J].

De Meijere, A ;

Von Zezschwitz, P ;

Bräse, S .

ACCOUNTS OF CHEMICAL RESEARCH, 2005, 38 (05) :413-422

[9] Functionalized alkylidenecyclopentenes by acid-catalyzed electrocyclic ring closure of (2Z)-(di)vinylallene acetals [J].

deLera, AR ;

Rey, JG ;

Hrovat, D ;

Iglesias, B ;

Lopez, S .

TETRAHEDRON LETTERS, 1997, 38 (42) :7425-7428

[10] Enantioselective synthesis of vinylcyclopropanes and vinylepoxides mediated by camphor-derived sulfur ylides: Rationale of enantioselectivity, scope, and limitation [J].

Deng, Xian-Ming ;

Cai, Ping ;

Ye, Song ;

Sun, Xiu-Li ;

Liao, Wei-Wei ;

Li, Kai ;

Tang, Yong ;

Wu, Yun-Dong ;

Dai, Li-Xin .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (30) :9730-9740

← 1 2 3 4 5 6 →