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

Synthesis of functionalized 3-aryl-3H-benzofuranone derivatives from aryl acetate via [3 + 2] annulation of 1,4-dihydroxy-2-naphthoic acid ester DOI
Huan Wang, Yuxiang Zhou, Ying Xie

et al.

Organic & Biomolecular Chemistry, Journal Year: 2023, Volume and Issue: 21(8), P. 1821 - 1826

Published: Jan. 1, 2023

A novel [3 + 2] cascade reaction of aryl acetate with 1,4-dihydroxy-2-naphthoic acid ester by cooperative catalysis isothiourea and vanadium is developed. The key step the that C1-ammonium enolates generated from will cycloadduct to 1,4-naphthoquinone intermediates. 3-Aryl-3H-benzofuranone derivatives can be prepared in medium good yields under mild conditions.

Language: Английский

Citations

4

Transition Metal‐Catalyzed Enantioselective Synthesis of Chiral Five‐ and Six‐Membered Benzo O‐heterocycles DOI
Yang Lu, Xiayu Liang, Yuyang Ding

et al.

The Chemical Record, Journal Year: 2023, Volume and Issue: 23(11)

Published: July 4, 2023

Enantiomerically enriched five- and six-membered benzo oxygen heterocycles are privileged architectures in functional organic molecules. Over the last several years, many effective methods have been established to access these compounds. However, comprehensive documents cover updated methodologies still highly demand. In this review, recent transition metal catalyzed transformations lead chiral presented. The mechanism chirality transfer or control processes also discussed details.

Language: Английский

Citations

4

Annulations involving p-benzoquinones: stereoselective synthesis of fused, spiro and bridged molecules DOI
Suven Das

New Journal of Chemistry, Journal Year: 2024, Volume and Issue: 48(18), P. 8243 - 8276

Published: Jan. 1, 2024

The present review summarizes the recent advances (2018–2023) in stereoselective annulation involving p -benzoquinones for construction of fused, spiro and bridged/cage frameworks.

Language: Английский

Citations

1

Copper Catalyzed [3+2] Annulation Reaction of Exocyclic Sulfonyl Enamides for the Synthesis of N,O‐Spiroketal and Spiroketal DOI

Wen‐Fu Cheng,

Shan‐Zeng Gao,

Yuchen Yang

et al.

Chemistry - A European Journal, Journal Year: 2024, Volume and Issue: 30(44)

Published: June 1, 2024

A copper-catalyzed [3+2] annulation reaction of exocyclic enamines/enol ethers with 1,4-benzoquinone esters has been developed, providing facile access to N,O-spiroketals and spiroketals under mild conditions broad substrate scope (26 examples, 71-94 % yields). Gram scale synthesis chemical transformations demonstrated that this method is potentially useful in the natural products drugs containing a N,O- spiroketal moiety. The chiral N,O-spiroketal could be obtained 98 ee after recrystallization, when SaBOX ligand was employed.

Language: Английский

Citations

1

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

Citations

6