Recent Advances on the Construction of Chiral Dihydrobenzofurans by Asymmetric [3+2] Cyclization Reactions of Phenols (Quinones) and Alkenes DOI Open Access

Lai Zhang,

Jian Xiao, Ya‐Wen Wang

et al.

Acta Chimica Sinica, Journal Year: 2022, Volume and Issue: 80(8), P. 1152 - 1152

Published: Jan. 1, 2022

Dihydrobenzofuran structural units are widely present in bioactive natural products, and therefore, this type of products have attracted extensive attention from synthetic organic chemists pharmaceutical chemists.In recent years, enantioselective formation unit, especially its C2 C3 vicinal chiral stereocenters, has always been one challenging problems the field methodology.Among some methods, construction optically active dihydrobenzofuran [3＋2] cyclizations phenols (quinones) olefins via asymmetric catalysis or induction by auxiliaries developed rapidly.In review, we summarized progress cyclization reactions with different types catalysts auxiliaries, emphasis on understanding control stereoselectivies these methods.Meanwhile, application total synthesis dihydrobenzofurans enabled was briefly introduced.Finally, future development trend [3＋ 2] analyzed, order to stimulate emergence highly efficient general catalytic system.

Language: Английский

Catalytic Asymmetric [3 + 2] Cycloaddition of Exocyclic Enol Ethers for the Synthesis of Spiroketals DOI Creative Commons
Fengcai Zhang, Yuqiao Zhou,

Hansen Zhao

et al.

Precision Chemistry, Journal Year: 2023, Volume and Issue: 1(7), P. 423 - 428

Published: July 24, 2023

An efficient synthesis of chiral benzannulated spiroketals via catalytic asymmetric [3 + 2] cycloaddition exocyclic enol ethers with p-quinones was achieved. The transformation enabled by a N,N′-dioxides/TmIII complex as the Lewis acid catalyst and afforded series enantiomerically enriched spiroketal derivatives in good yields (up to 99%) enantioselectivities 98% ee). Topographic steric maps distribution buried volumes catalysts Cavallo's SambVca 2 tool were used elucidate enantioinduction raised ligands metal ions.

Language: Английский

Citations

9
Rapid Construction of Enantioenriched Benzofurochromanes by SaBOX/Copper(II) Catalyzed Enantioselective [3 + 2] Annulation of γ-Chromenes with Quinones DOI
Yang Chen,

Geng-Xie Li,

Ai‐Qing Peng

et al.

Organic Letters, Journal Year: 2022, Volume and Issue: 24(30), P. 5525 - 5529

Published: July 25, 2022

A rapid construction of enantioenriched benzofurochromanes was developed by SaBOX/copper(II) catalyzed enantioselective [3 + 2] annulation γ-chromenes with quinones. This process takes advantage the simple starting materials and a highly efficient chiral catalyst system, leading to variety in up 96% yield 97% ee.

Language: Английский

Citations

13
Visible-light-driven [3 + 2] cyclization of phenols with indoles and olefins using recyclable Ag3PO4 nanoparticles DOI
Lirong Guo, Guanjie Chen, Haibin Li

et al.

Green Chemistry, Journal Year: 2023, Volume and Issue: 25(18), P. 7102 - 7108

Published: Jan. 1, 2023

Ag 3 PO 4 was used in the oxidative [3 + 2] annulation of phenols with styrenes and indoles under visible-light irradiation. A number structurally diverse benzofuroindolines 2,3-dihydrobenzofurans were synthesized.

Language: Английский

Citations

7
Enantioselective Synthesis of 2,3,3a,8a-Tetrahydrofuro[2,3-b]benzofuran Scaffolds Enabled by Cu(II)/SPDO-Catalyzed [3+2] Cycloaddition of 2,3-Dihydrofuran and Quinone Esters DOI

Jin‐Xin Zhu,

Jin‐Miao Tian,

Yaoyao Chen

et al.

The Journal of Organic Chemistry, Journal Year: 2023, Volume and Issue: 88(20), P. 14670 - 14675

Published: Oct. 10, 2023

An asymmetric [3+2] cycloaddition of quinone esters with 2,3-dihydrofuran has been realized via a newly developed Cu(II)/SPDO complex. It provides straightforward access to 2,3,3a,8a-tetrahydrofuro[2,3-b]benzofurans (TFB) high enantioselectivity (up 97.5:2.5 er) and diastereoselectivity (all >20:1 dr). The resulting adducts contain two adjacent stereocenters continuously functionalized benzene ring. Additionally, this transformation could be easily performed on gram scale, allowing for expedient synthesis natural dihydroaflatoxin D2 aflatoxin B2.

Language: Английский

Citations

7
Asymmetric Synthesis of Hydrodibenzofurans from Norcaradienes: Kinetic Resolution via [3 + 2] Cycloaddition with Quinones DOI
Siyuan Wang, Lichao Ning, Zhiqiang Li

et al.

Organic Letters, Journal Year: 2024, Volume and Issue: 26(18), P. 3844 - 3849

Published: April 25, 2024

The catalytic asymmetric [3 + 2] cycloaddition of racemic norcaradienes with quinones to construct multicyclic hydrodibenzofurans was achieved by the use chiral N,N′-dioxide/metal complex catalysts. Kinetic resolution accompanied partial racemization occurred, and one enantiomer in prior acted as C2 synthon participate diastereoselective cycloaddition. An enantiodivergent synthesis via a switch metal ions observed when naphthoquinone used partner. DFT calculations revealed profiles processes.

Language: Английский

Citations

2
Urazoles as Heterocyclic Directing Groups in Ru(II)-Catalyzed Annulation of N–H/C–H Bonds with Vinylene Carbonate DOI
Jungmin Kang, Ji‐Hye Park, Pargat Singh

et al.

The Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: unknown

Published: Dec. 5, 2024

The development of novel directing groups is a valuable strategy to secure the advancement catalytic C-H functionalization. To illustrate feasibility urazoles as heterocyclic groups, we herein present ruthenium(II)-catalyzed annulation N-H/C-H bonds on

Language: Английский

Citations

2
Visible-Light-Induced Regioselective Functionalization of α-Olefin: Development of One-Pot Photo-Synthesis of C3-Substituted Dihydrobenzofurans DOI
Saki Maejima, Eiji Yamaguchi,

Akichika Itoh

et al.

Organic Letters, Journal Year: 2023, Volume and Issue: 25(11), P. 1856 - 1861

Published: March 3, 2023

A method for the catalytic regioselective synthesis of C3-substituted dihydrobenzofurans (DHBs) via [2 + 2] photocycloaddition alkene and p-benzoquinone is developed. This realizes rapid DHBs with readily available substrates simple reaction conditions by using Lewis acid B(C6F5)3 base P(o-tol)3 as a catalyst in combination classical Paternò-Büchi reaction.

Language: Английский

Citations

6
Catalytic Asymmetric Polycyclization of Tertiary Enamides with Silyl Enol Ethers: Total Synthesis of (−)-Cephalocyclidin A DOI

Qing‐Bo Zhuang,

Jin-Rui Tian,

Ka Lu

et al.

Journal of the American Chemical Society, Journal Year: 2023, Volume and Issue: 145(49), P. 26550 - 26556

Published: Nov. 29, 2023

A catalytic enantioselective polycyclization of tertiary enamides with terminal silyl enol ethers has been developed by virtue Cu(OTf)2 catalysis a novel spiropyrroline-derived oxazole (SPDO) ligand. This tandem reaction offers an effective approach to assemble bicyclic and tricyclic N-heterocycles bearing both aza- oxa-quaternary stereogenic centers, which are primal subunits in range natural alkaloids. Strategic application this methodology late-stage radical cyclization as key steps have showcased the concise total synthesis (−)-cephalocyclidin A.

Language: Английский

Citations

6
Electrochemical Dearomative Amination of Phenol Derivatives: Access to Spirooxazolidinones DOI

Jin‐Lin Wan,

Jing‐Mei Huang

Advanced Synthesis & Catalysis, Journal Year: 2023, Volume and Issue: 365(8), P. 1211 - 1216

Published: March 23, 2023

Abstract An electrochemical oxidative approach to spirooxazolidinones from phenol derivatives via intramolecular dearomative amination reactions is developed. This reaction proceeds without metal catalysts and external chemical oxidants, shows broad substrate scope diverse functional group compatibility. The synthetic utility of this strategy further exhibited by the gram‐scale synthesis late‐stage functionalization. By slightly tunning conditions, alcohols (1°, 2° 3°) can be afforded derivatives, which a good for deprotection para ‐methoxyphenyl (PMP) recover alcohol function. magnified image

Language: Английский

Citations

5
Recent advances on copper-catalyzed asymmetric synthesis and their potential biological applications DOI Creative Commons

Hoorub Ahmad,

Muhammad Bılal, Tahir Maqbool

et al.

Journal of Saudi Chemical Society, Journal Year: 2023, Volume and Issue: 27(4), P. 101658 - 101658

Published: May 27, 2023

An asymmetric catalysis is a form of catalytic reaction wherein chiral catalyst controls the production molecule to favour synthesis one stereoisomer over another. It's good way make stereoisomeric molecules for pharmacological purposes. Among transition metals, copper cost-effective, plentiful, and less poisonous metal. This review focused on transformations in last fifteen years.

Language: Английский

Citations

5