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
Banaag, April R.
Tius, Marcus A.
[J]. JOURNAL OF ORGANIC CHEMISTRY, 2008, 73 (21) : 8133 - 8141
[3] Design of chiral auxiliaries for the allene ether Nazarov cyclization
Banaag, April R.
Tius, Marcus A.
[J]. 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
Cao, Peng
Li, Chuan-Ying
Kang, Yan-Biao
Xie, Zuowei
Sun, Xiu-Li
Tang, Yong
[J]. JOURNAL OF ORGANIC CHEMISTRY, 2007, 72 (17) : 6628 - 6630
[5] Tandem and domino catalytic strategies for enantioselective synthesis
Chapman, Christopher J.
Frost, Christopher G.
[J]. SYNTHESIS-STUTTGART, 2007, (01): : 1 - 21
[6] Gold-catalyzed cycloisomerization of 1,5-allenynes via dual activation of an ene reaction
Cheong, Paul Ha-Yeon
Morganelli, Philip
Luzung, Michael R.
Houk, K. N.
Toste, F. Dean
[J]. 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
Crone, Benedikt
Kirsch, Stefan F.
[J]. 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
De Meijere, A
Von Zezschwitz, P
Bräse, S
[J]. ACCOUNTS OF CHEMICAL RESEARCH, 2005, 38 (05) : 413 - 422
[9] Functionalized alkylidenecyclopentenes by acid-catalyzed electrocyclic ring closure of (2Z)-(di)vinylallene acetals
deLera, AR
Rey, JG
Hrovat, D
Iglesias, B
Lopez, S
[J]. 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
Deng, Xian-Ming
Cai, Ping
Ye, Song
Sun, Xiu-Li
Liao, Wei-Wei
Li, Kai
Tang, Yong
Wu, Yun-Dong
Dai, Li-Xin
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (30) : 9730 - 9740

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