Strategic 1,9-Proton-Transfer-Driven Cycloaddition: Synthesis and Stereoselective Contraction of Nine-Membered Heterocycles DOI

Sekwang Baek,

Ju Young Lee,

Min Jae Kang

и другие.

ACS Catalysis, Год журнала: 2024, Номер 14(21), С. 16105 - 16114

Опубликована: Окт. 17, 2024

We introduce a phosphine-catalyzed cycloaddition involving unprecedented long-range intramolecular proton transfer, facilitating the synthesis of nine-membered heterocycles, which are privileged structures in natural products, as well potent pharmacophores. Experimental and computational studies revealed that enamide tether N-aromatic zwitterion directly enables regioselective transfer to proceed independently outer-sphere shuttling. This understanding selective has led improved efficiency regioselectivity desired 1,9-proton reaction under anhydrous conditions, thereby advancing development higher-order reactions. Further stereoselective contraction synthesized cyclic compounds using 3-aza-Cope rearrangement demonstrates synthetic versatility our approach. The findings this study not only advance general mechanism but also broaden its practical utility various chemical fields.

Язык: Английский

Recent advances of Pd-π-allyl zwitterions in cycloaddition reactions DOI
Juan Du, Yunfan Li, Chang‐Hua Ding

и другие.

Chinese Chemical Letters, Год журнала: 2023, Номер 34(11), С. 108401 - 108401

Опубликована: Март 30, 2023

Язык: Английский

Процитировано

25

Pd-Catalyzed Ligand-Directed Divergent Cycloaddition of Cyclic 1-Azadienes with Oxo-1,4-dipoles DOI

Hongling Xie,

Lei Chen, Zhengyu Han

и другие.

Organic Letters, Год журнала: 2023, Номер 25(27), С. 5011 - 5016

Опубликована: Июнь 29, 2023

Ligand-directed divergent synthesis (LDS) is an important synthetic tool for the preparation of structurally diverse organic molecules without tedious steps to modify substrates. Herein, we introduce realization 3,4-, 1,2-, and 1,4-cyclization benzo[d]isothiazole-1,1-dioxide-fused azadienes (BDAs) through LDS, leading tetrahydro-2H-pyrans, oxazinanes, tetrahydro-2H-1,5-oxazocines, respectively. Using phosphinooxazoline (PHOX) ligands, have developed a [4 + 2] cycloaddition between BDAs substituted 2-alkylidenetrimethylene carbonates, providing access multi-substituted chiral tetrahydro-2H-pyrans in good yields with excellent enantio-, diastereo-, regioselectivities.

Язык: Английский

Процитировано

23

Copper-Catalyzed Enantioselective Formal [4 + 1] and [3 + 3] Cycloaddition of Ethynylethylene Carbonates DOI

Haihui Zhu,

Lixia Xu,

Biao Zhu

и другие.

Organic Letters, Год журнала: 2023, Номер 25(51), С. 9213 - 9218

Опубликована: Дек. 15, 2023

Herein we employed ethynylethylene carbonates (EECs) to achieve formal [4 + 1] and [3 3] cycloaddition with cyclic 1,3-dicarbonyl compounds. On one hand, EECs styryl substitution could undergo a remotely controlled enantioselective reaction. This reaction exhibits good chemoselectivity, regioselectivity, enantioselectivity. In addition, of compounds was also achieved, leading series 4H-pyrans impressive chemoselectivity

Язык: Английский

Процитировано

21

Tandem Allylic Amination/oxa-Michael Addition of Vinyl Methylene Cyclic Carbonates via Palladium-Organo Relay Catalysis DOI

Zhenkun Yang,

Yu Bao,

Jiaxin Huang

и другие.

Organic Letters, Год журнала: 2023, Номер 25(30), С. 5624 - 5629

Опубликована: Июль 24, 2023

A tandem allylic amination/oxa-Michael addition of vinyl methylene cyclic carbonates (VMCCs) has been developed to construct heterocycles by single palladium catalysis or palladium-organo relay catalysis. In this process, the bisnucleophiles first underwent regioselective amination, and then second nucleophilic group further completed hetero-Michael reaction form a series heterocycles. Among them, chiral 3,4-dihydro-2H-benzo[b][1,4]oxazines could be produced in medium high yield with good enantioselectivity under

Язык: Английский

Процитировано

11

Palladium‐Catalyzed [4+2] and [6+2] Dipolar Cycloadditions for the Construction of Benzo[d]isothiazole 1,1‐Dioxide Fused 1,3‐Oxazinanes and 1,3‐Oxazocanes DOI Open Access
Lei Chen,

Hongling Xie,

Yu Xue

и другие.

Chinese Journal of Chemistry, Год журнала: 2023, Номер 42(8), С. 829 - 834

Опубликована: Дек. 8, 2023

Comprehensive Summary The Pd‐catalyzed dipolar cycloaddition represents a significant synthetic strategy for the construction of useful heterocyclic compounds. This study developed [4+2] and [6+2] reactions benzo[ d ]isothiazole 1,1‐dioxides (BDs) leading to synthesis BD‐fused 1,3‐oxazinane 1,3‐oxazocane derivatives, respectively. In particular, 1,3‐oxazinanes demonstrated regio‐ enantioselective characteristics, resulting in products with good yields, enantioselectivity regioselectivity (if applicable). Furthermore, reaction this work represented first medium‐sized ring compounds based on BDs.

Язык: Английский

Процитировано

9

Synthesis of medium-sized heterocycles from oxetanes based on an allylic amination/ring-opening strategy DOI
Jixing Li, Ming Fang,

Maoyan Liao

и другие.

Chemical Communications, Год журнала: 2023, Номер 59(97), С. 14467 - 14470

Опубликована: Янв. 1, 2023

The construction of medium-sized ring compounds has been a prominent research area in synthetic chemistry. In this study, we developed tandem strategy that combines allylic amination and ring-opening oxetanes to synthesize heterocycles. Specifically, N-aryl oxetan-3-amines undergo with zwitterionic π-allylpalladium, followed by intramolecular ring-opening, resulting the formation Notably, are able achieve synthesis 7-8 membered heterocycles moderate good yields employing different types π-allylpalladium species.

Язык: Английский

Процитировано

8

Construction of diverse polycyclic N-heterocycles via cascade allylic amination/Diels–Alder reaction DOI

Zhenkun Yang,

Hongling Xie,

Luning Tang

и другие.

Chemical Communications, Год журнала: 2022, Номер 58(95), С. 13258 - 13261

Опубликована: Янв. 1, 2022

An efficient cascade approach for the construction of nitrogen-containing polycyclic compounds from amines tethered with an alkenyl (or alkynyl) group and divinyl carbonates is described.

Язык: Английский

Процитировано

12

Palladium-catalyzed [4+4] cycloaddition of 2-pyrones with 2-alkylidenetrimethylene carbonates: access to bridged eight-membered oxygen heterocycles DOI

Huawei Lin,

Biming Mao, Bing Han

и другие.

Organic Chemistry Frontiers, Год журнала: 2024, Номер 11(10), С. 2864 - 2869

Опубликована: Янв. 1, 2024

A novel palladium-catalyzed [4 + 4] cycloaddition of 2-pyrones with 2-alkylidenetrimethylene carbonates has been developed for the synthesis bridged eight-membered oxygen heterocycles in good yields and excellent stereoselectivities.

Язык: Английский

Процитировано

2

Studies on the [4 + 2] cycloaddition and allylic substitution of indole-fused zwitterionic π-allylpalladium DOI
Zhengyu Han, Yu Xue, Xiang Li

и другие.

Organic & Biomolecular Chemistry, Год журнала: 2023, Номер 21(40), С. 8162 - 8169

Опубликована: Янв. 1, 2023

The zwitterionic π-allylpalladium species, also known as dipoles, are important synthons widely used in various reactions including cycloaddition and allylic substitution. This study reported the development of a new indole-fused precursor compound its application [4 + 2] substitution reactions. As result, synthesis pyrrolo[3,2,1-ij]quinazolin-3-one 7-vinyl indole compounds was achieved with moderate to good yields. Notably, reaction exhibited excellent regio- stereoselectivity.

Язык: Английский

Процитировано

5

A palladium-catalyzed decarboxylative (5 + 5) cyclization reaction of vinyloxazolidine-2,4-diones: access to ten-membered N,O-containing heterocycles DOI
Xiaohui Fu, Juan Liao, Zhen‐Hua Wang

и другие.

Organic Chemistry Frontiers, Год журнала: 2024, Номер 11(15), С. 4131 - 4137

Опубликована: Янв. 1, 2024

A palladium-catalyzed decarboxylative (5 + 5) cyclization reaction of vinyloxazolidine-2,4-diones for the synthesis ten-membered N,O-containing heterocycles is disclosed.

Язык: Английский

Процитировано

1