Diastereoselective Synthesis of Dearomatic 2‐oxa‐7‐azaspiro[4.5]decane Derivatives through Gold and Palladium Relay Catalytic Tandem Cyclization of Enynamides with Vinyl Benzoxazinanones DOI
Jiaming Xu, Yanfeng Gao, Xin Gao

и другие.

Advanced Synthesis & Catalysis, Год журнала: 2024, Номер 366(22), С. 4778 - 4785

Опубликована: Авг. 14, 2024

Abstract We present a diastereoselective Au/Pd relay catalytic tandem cyclization reaction to produce dearomatic 2‐oxa‐7‐azaspiro[4.5]decane derivatives under mild conditions. This process involves generating furan‐derived azadiene from readily available enynamide, followed by [2+4] cycloaddition with Pd‐ π ‐allyl dipole decarboxylated vinyl benzoxazinanone. Our method efficiently constructs the spiro[4.5]decane skeleton, achieving yields ranging 31–97% and diastereoselectivities 6:1 dr >20:1 across 34 examples. research introduces new sites for azadienes as 1,2‐dipoles offers reliable approach constructing oxa‐azaspiro[4.5]decane frameworks.

Язык: Английский

Convenient synthesis of chromene-fused spirocyclopentane-1,2-dioxindoles via base promoted annulation reaction DOI
Kun Huang, Ting Tang, Ying Han

и другие.

Tetrahedron Letters, Год журнала: 2025, Номер 156, С. 155455 - 155455

Опубликована: Янв. 8, 2025

Язык: Английский

Процитировано

0
Rapid construction of S-containing spirooxindoles and dispirooxindoles via annulation of MBH maleimides of isatins DOI
Kun Huang, Kaihua Zhang,

Ziying Xiao

и другие.

Tetrahedron Letters, Год журнала: 2025, Номер 156, С. 155452 - 155452

Опубликована: Янв. 13, 2025

Язык: Английский

Процитировано

0
Molecular diversity of the reactions of MBH carbonates of isatins and various nucleophiles DOI Creative Commons

Ziying Xiao,

Jing Sun,

Chao‐Guo Yan

и другие.

Beilstein Journal of Organic Chemistry, Год журнала: 2025, Номер 21, С. 286 - 295

Опубликована: Фев. 6, 2025

In this paper, the nucleophilic substitution reactions of various N- and P-containing nucleophiles to MBH carbonates isatins were investigated. Diverse functionalized 3-substituted oxindole derivatives successfully prepared in satisfactory yields with high diastereoselectivity. addition, base-promoted dimerization isatin afforded ethylene-bridged bis(3-methylene)oxindole nearly 4:1 diastereomeric ratios. The relative configurations polycyclic compounds clearly elucidated by determination several single crystal structures.

Язык: Английский

Процитировано

0
Merging Enantioselective Lewis Base Organocatalysis and Gold(I) Catalysis: A One-Pot Access to Chiral-Fused Polycyclic Compounds DOI

Rémi Pereira,

Pierre Locquet,

Aurélien Blanc

и другие.

The Journal of Organic Chemistry, Год журнала: 2025, Номер unknown

Опубликована: Фев. 21, 2025

Reported herein is a route to functionalized chiral heteroaromatic polycyclic compounds leveraging two unfriendly catalytic cycles in one-pot sequential process. α-Heteroaromatic-γ-butyrolactones were engaged highly regio-, diastereo-, and enantio-selective Lewis base asymmetric allylic alkylation (AAA) with alkyne-functionalized Morita–Baylis–Hillman (MBH) carbonates. Gratefully, due the low catalyst loading, subsequent gold-catalyzed Friedel–Crafts type cyclization, entailing formation of fused compounds, proceeded efficiently, affording structurally complex, enantioenriched products.

Язык: Английский

Процитировано

0
Diastereoselective Synthesis of Dearomatic 2‐oxa‐7‐azaspiro[4.5]decane Derivatives through Gold and Palladium Relay Catalytic Tandem Cyclization of Enynamides with Vinyl Benzoxazinanones DOI
Jiaming Xu, Yanfeng Gao, Xin Gao

и другие.

Advanced Synthesis & Catalysis, Год журнала: 2024, Номер 366(22), С. 4778 - 4785

Опубликована: Авг. 14, 2024

Abstract We present a diastereoselective Au/Pd relay catalytic tandem cyclization reaction to produce dearomatic 2‐oxa‐7‐azaspiro[4.5]decane derivatives under mild conditions. This process involves generating furan‐derived azadiene from readily available enynamide, followed by [2+4] cycloaddition with Pd‐ π ‐allyl dipole decarboxylated vinyl benzoxazinanone. Our method efficiently constructs the spiro[4.5]decane skeleton, achieving yields ranging 31–97% and diastereoselectivities 6:1 dr >20:1 across 34 examples. research introduces new sites for azadienes as 1,2‐dipoles offers reliable approach constructing oxa‐azaspiro[4.5]decane frameworks.

Язык: Английский

Процитировано

0