Titanium-catalyzed highly stereoselective anti-Markovnikov intermolecular hydroalkoxylation of alkynes to prepare Z-enol ethers

文献情報

出版日 2023-11-15

DOI 10.1039/D3OB01514A

インパクトファクター 3.876

著者

Yang Wang, Biao Ma, Yingning Mao, Zhihui Wang, Jinsong Peng, Chunxia Chen, Zhanyu Li

原文を見る

要旨

Enol ethers are essential synthetic frameworks and widely applied in organic synthesis; however, high regio- and stereo-selective access to enol ethers remains challenging. Herein, we report a titanium-catalyzed stereospecific anti-Markovnikov hydroalkoxylation reaction of alkynes for the synthesis of Z-enol ethers with excellent functional group tolerance and yields. Mechanistic studies showed that the titanium coordinates with the alkyne and then an oxygen anion attacks the π-bond of the alkyne from the backside to provide a trans-oxygen metallation intermediate, which accounts for the high Z-stereoselectivity. Furthermore, Z-enol ethers could be applied as a kind of synthon for late-stage transformations and gram-scale synthesis, which demonstrates their potential value in organic synthesis.

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.

Titanium-catalyzed highly stereoselective anti-Markovnikov intermolecular hydroalkoxylation of alkynes to prepare Z-enol ethers

文献情報

おすすめジャーナル

関連文献

A total synthesis of (±)-α-cyclopiazonic acid using a cationic cascade

Concomitant polymorphs of 2,2′,6,6′-tetramethyl-4,4′-terphenyldiol: the β-quinol network reproduced in a metastable polymorph

Front cover

Rapid and effective labeling of brain tissue using TAT-conjugated CdS∶Mn/ZnS quantum dots

Enhancement of electrochemical and photoelectrochemical properties of fibrous Zn and ZnO electrodes

Achiral molecules in non-centrosymmetric space groups

A readily prepared neutral heterobimetallic titanium(iv)–rhodium(i) catalyst for intramolecular hydroacylation

Putrescine homologues control silica morphogenesis by electrostatic interactions and the hydrophobic effect

Mono- and digallane complexes of a tridentate amido-diamine ligand

A novel heterogeneous acid-activated clay supported copper catalyst for the photobleaching and degradation of textile organic pollutant using photo-Fenton-like reaction

こちらもおすすめ

6-苄基-6,7-二氢-5H-吡咯并3,4-b吡啶とは何ですか？

半硫酸奎宁单水水合物はどのように保存すればよいですか？

D-核糖-5-リン酸二ナトリウムとは何ですか？

異丙基肼はどの業界で使用されていますか？

3-乙酰基-4-羟基喹啉-2(1H)-酮はどのように合成されますか？

Bobcat339はどのように保存すればよいですか？

5-溴-4-甲基-1H-吲唑とは何ですか？

3-(4メトキシフェニル)オキテナン-3カーボイル酸の代替品はありますか？

3-イリドオキシピロロ[2,3-b]ピリジン-5-カルボキシlic酸は安全ですか？

3-氟-4- iodobenol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

3-[(3R,4R)-3-[(6-aminopyrimidin-4-yl)-methyl-amino]-4-methyl-1-piperidyl]-3-oxo-propanenitrile

4,6-O-Ethylidene-D-glucopyranose

5-(Methoxymethoxy)-2-methylphenylboronic acid

(1R,6R)-6-({[(2-Methyl-2-propanyl)oxy]carbonyl}amino)-3-cyclohexene-1-carboxylic acid

5-(4-Fluorophenyl)-1,3,4-oxadiazol-2(3H)-one

おすすめサプライヤー