δ-Cyano substituted para-quinone methides enable access to unsymmetric tri- and tetraarylmethanes containing all-carbon quaternary stereocenters

文献情報

出版日 2020-04-25

DOI 10.1039/D0OB00551G

インパクトファクター 3.876

著者

Yue Qi, Fang Zhang, Lin Wang, Aili Feng, Rongxiu Zhu, Shutao Sun, Wei Li, Lei Liu

原文を見る

要旨

para-Quinone methides bearing an electron-withdrawing cyano group at the exocyclic methylene δ-position were identified as valuable 1,6-conjugate addition building blocks for acyclic all-carbon quaternary stereocenter construction. A wide variety of electron-rich arenes as nucleophiles were tolerated, effectively furnishing diverse unsymmetrical triarylmethanes bearing all-carbon quaternary stereocenters. The robust transformable abilities of the cyano group provide a platform to access other valuable functional group-containing unsymmetrical tri- and tetraarylmethanes that are otherwise difficult to be prepared. Computational studies supported the hypothesis that the cyano group at the δ-position tunes the molecular electron-density distribution, and the stability of para-quinone methides is enhanced by lowering their polymerizability.

掲載誌

Organic & Biomolecular Chemistry

CiteScore: 3.4

自己引用率: 10.3%

年間論文数: 1041

Organic & Biomolecular Chemistry (OBC) publishes original and high impact research and reviews in organic chemistry. We welcome research that shows new or significantly improved protocols or methodologies in total synthesis, synthetic methodology or physical and theoretical organic chemistry as well as research that shows a significant advance in the organic chemistry or molecular design aspects of chemical biology, catalysis, supramolecular and macromolecular chemistry, theoretical chemistry, mechanism-oriented physical organic chemistry, medicinal chemistry or natural products. Articles published in the journal should report new work which makes a highly-significant impact in the field. Routine and incremental work is generally not suitable for publication in the journal. More details about key areas of our scope are below. In all cases authors should include in their article clear rationale for why their research has been carried out.

δ-Cyano substituted para-quinone methides enable access to unsymmetric tri- and tetraarylmethanes containing all-carbon quaternary stereocenters

文献情報

おすすめジャーナル

関連文献

Wilsonglucinols A–C, homoadamantane-type polycyclic polyprenylated acylphloroglucinols with unusual fused epoxy ring skeletons from Hypericum wilsonii

Substrate-directed chemo- and regioselective synthesis of polyfunctionalized trifluoromethylarenes via organocatalytic benzannulation

Inside front cover

Stereoselective assembly of 3,4-epoxypyrrolines via nucleophilic addition induced domino cyclization of 6-halo-1-oxa-4-azahexatrienes

Ni-Catalyzed electrophile driven regioselective arylative cyclization of ortho-functional diaryl acetylenes for the synthesis of pyridine and indene derivatives

A diastereoselective approach to amino alcohols and application for divergent synthesis of dolastatin 10

Metal-free insertion of sulfur dioxide with aryl iodides under ultraviolet irradiation: direct access to sulfonated cyclic compounds

Phomeroids A and B: two novel cytotoxic meroterpenoids from the deep-sea-derived fungus Phomopsis tersa FS441

Lewis acid-catalyzed tandem cyclization of in situ generated o-quinone methides and arylsulfonyl hydrazides for a one-pot entry to 3-sulfonylbenzofurans

Synthesis of α-cyano sulfone via thermal rearrangement of 1,4-disubstituted triazole mediated by carbene and radical species

こちらもおすすめ

3-(5-フェニル-2-ファイル)-プロパン酸の市場動向や研究トレンドはどうですか？

3- Chloro-1H-indazol-5-olはどのように保存すればよいですか？

二茂鐵是安全的吗？

L-(1-~13~C)メチオニンの市場動向や研究トレンドはどうですか？

1,3-フェニレンビスメチレンビスアクリレートは安全ですか？

丹参醇Aはどのように保存すればよいですか？

4-メチル-2-(1,1,1-三フロロ-2-メチルプロパニル)ピリドインとは何ですか？

N-フェニルベンジル-2-クロロ酢氨を取り扱う際の実験室安全事項は何ですか？

UCN-02を取り扱う際の実験室安全事項は何ですか？

N-[3-[2-(二甲基氨基)乙氧基]-4-甲氧基苯基]-2'-甲基-4'-(5-甲基-1,2,4-恶二唑-3-基)-[1,1'-联苯]-4-甲酰胺を取り扱う際の実験室安全事項は何ですか？

掲載誌

Organic & Biomolecular Chemistry

おすすめ化合物

N,N-Diethyl-2-propyn-1-amine sulfate (1:1)

O,O-Dimethyl hydrogen phosphorodithioate

2,6-dichloropyridin-1-ium-1-olate

5-Bromoimidazo[1,2-a]pyridine

(3R,4R)-3,4-Dihydroxydihydro-2(3H)-furanone

おすすめサプライヤー