Synthesis of γ-Aryl Medium-Sized Cyclic Enones by a Domino 4π-Electrocyclic Reaction/Heck-Matsuda Arylation Sequence at Ambient Temperature

被引：1

作者：

Ito, Tomohiro ^{[1
]}

Takeuchi, Nao ^{[1
]}

Yamaoka, Yousuke ^{[1
]}

Takikawa, Hiroshi ^{[1
]}

Takasu, Kiyosei ^{[1
]}

机构：

[1] Kyoto Univ, Grad Sch Pharmaceut Sci, Sakyo Ku, Kyoto 6068501, Japan

来源：

SYNLETT | 2023年 / 34卷 / 11期

关键词：

medium-sized rings; electrocyclic reaction; Heck-Matsuda reaction; arylation; cyclobutenes; chirality transfer; ALPHA; BETA-UNSATURATED CARBONYL-COMPOUNDS; REACTIVITY; CASCADE; KETONES; SALTS; IONS;

D O I：

10.1055/a-2024-4675

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Bicyclo[n.2.0]cyclobutenes were transformed into medium-sized cyclic y-aryl enones by using a cationic aryl palladium(II) species generated from a diazonium salt. The reaction proceeded at ambient temperature by capturing the cis ,trans-cycloalkadiene intermediate generated through a conrotatory 4m-electrocyclic ring-opening reaction, followed by a Heck-Matsuda arylation sequence. Optically pure y aryl enones were also synthesized by using a point-to-planar-to-point chirality-transfer process.

引用

页码：1275 / 1279

页数：5

共 37 条

[1] [Anonymous], CCDC 2234158 CON SUP
[2] [Anonymous], CURR ADDR SCH PHARM
[3] An Arylative Ring Expansion Cascade of Fused Cyclobutenes via Short-Lived Intermediates with Planar Chirality
Arichi, Norihito
Yamada, Ken-ichi
Yamaoka, Yousuke
Takasu, Kiyosei
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2015, 137 (30) : 9579 - 9582
[4] Cu-Catalyzed Stereoselective γ-Alkylation of Enones
Chen, Xiaohong
Liu, Xiaoguang
Mohr, Justin T.
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2016, 138 (20) : 6364 - 6367
[5] Direct Regioselective γ-Amination of Enones
Chen, Xiaohong
Liu, Xiaoguang
Mohr, Justin T.
[J]. ORGANIC LETTERS, 2016, 18 (04) : 716 - 719
[6] Christoffers J, 2000, EUR J ORG CHEM, V2000, P1977
[7] [2+2] CYCLOADDITION OF ETHYL PROPIOLATE AND SILYL ENOL ETHERS
CLARK, RD
UNTCH, KG
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1979, 44 (02) : 248 - 253
[8] Cyclopentenone: a special moiety for anticancer drug design
Conti, Matteo
[J]. ANTI-CANCER DRUGS, 2006, 17 (09) : 1017 - 1022
[9] Das M., 2015, CURR BIOACT COMPD, V11, P239, DOI DOI 10.2174/157340721104151230104138
[10] Asymmetric Domino Reaction of α,β-Unsaturated Aldehydes and α-Acyl α,β-Unsaturated Cyclic Ketones Catalyzed by Diphenylprolinol Silyl Ether
Hayashi, Yujiro
Suga, Yurina
Umekubo, Nariyoshi
[J]. ORGANIC LETTERS, 2020, 22 (21) : 8603 - 8607

← 1 2 3 4 →