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 3 条

[1] Synthesis of Functionalized Medium-Sized trans-Cycloalkenes by 4π Electrocyclic Ring Opening/Alkylation Sequence
Ito, Tomohiro
Tsutsumi, Masaki
Yamada, Ken-ichi
Takikawa, Hiroshi
Yamaoka, Yousuke
Takasu, Kiyosei
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2019, 58 (34) : 11836 - 11840
[2] Stereoselective Synthesis of Unsymmetrical β,β-Diarylacrylates by a Heck-Matsuda Reaction: Versatile Building Blocks for Asymmetric Synthesis of β,β-Diphenylpropanoates, 3-Aryl-indole, and 4-Aryl-3,4-dihydro-quinolin-2-one and Formal Synthesis of (-)-Indatraline
Taylor, Jason G.
Correia, Carlos Roque D.
JOURNAL OF ORGANIC CHEMISTRY, 2011, 76 (03): : 857 - 869
[3] Stereoselective Synthesis of Unsymmetrical β,β-Diarylacrylates by a Heck-Matsuda Reaction: Versatile Building Blocks for Asymmetric Synthesis of β,β-Diphenylpropanoates, 3-Aryl-indole, and 4-Aryl-3,4-dihydro-quinolin-2-one and Formal Synthesis of (-)-Indatraline (vol 76, pg 857, 2011)
Taylor, Jason G.
Correia, Carlos Roque D.
JOURNAL OF ORGANIC CHEMISTRY, 2012, 77 (11): : 5220 - 5220

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