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

et al.

Advanced Synthesis & Catalysis, Journal Year: 2024, Volume and Issue: 366(22), P. 4778 - 4785

Published: Aug. 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.

Language: Английский

Highly Enantioselective Organocatalytic Mannich Reaction of α-Benzylidene Succinimides with N-Boc Imines: Experimental and Theoretical Studies DOI

K Kimura,

Yuto Shimizu,

Katsuya Kanno

et al.

The Journal of Organic Chemistry, Journal Year: 2025, Volume and Issue: unknown

Published: March 24, 2025

The development of efficient and practical methods for the construction chiral succinimide frameworks, which are backbone various natural products widely studied in field pharmaceuticals, attracts considerable research attention. In this study, an asymmetric Mannich reaction α-benzylidene succinimides with N-Boc imines was successfully performed using a bifunctional squaramide-type organocatalyst derived from quinine, affording corresponding adduct two contiguous stereocenters high yields (up to 98%) diastereoselectivities >20:1 dr) excellent enantioselectivities 99% ee). This protocol provides direct approach prepare derivatives simple starting material. Density Functional Theory (DFT) calculations conformational search autosampling program revealed that enantioselectivity profile dominated by deformation organocatalyst.

Language: Английский

Citations

0
Base-Promoted Chemodivergent Construction of 2H-Chromen-2-one and Chromeno[2,3-c]pyrrole Scaffolds from para-Quinone Methides and α-Alkylidene Succinimides DOI

Km Roshani,

Mohammad Saim Raza,

Rama Krishna Peddinti

et al.

Organic Letters, Journal Year: 2024, Volume and Issue: 26(42), P. 9114 - 9119

Published: Oct. 11, 2024

Herein, we evolve a base-promoted synthesis of 2

Language: Английский

Citations

1
Phosphine-Catalyzed [4 + 1] Annulation of β’-Acetoxy Allenoate with α-Alkylidene Succinimides: Access to Functionalized Spirosuccinimide Derivatives DOI
Chunjie Ni,

Zhanhang Liang,

Xiaojuan Xu

et al.

The Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 89(22), P. 16711 - 16720

Published: Oct. 31, 2024

A phosphine-catalyzed [4 + 1] annulation of β'-acetoxy allenoate with α-alkylidene succinimides is described. This method demonstrates the nucleophilic dialkylation and cyclization succinimides, resulting in formation functionalized spirosuccinimide derivatives. The reaction exhibits a wide substrate scope yields ranging from moderate to excellent under optimized conditions. In addition, biological evaluation indicates that cycloadduct 3u presents satisfied inhibitory activities for three human cancer cell lines (HCT116, A549, HepG2).

Language: Английский

Citations

1
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

et al.

Advanced Synthesis & Catalysis, Journal Year: 2024, Volume and Issue: 366(22), P. 4778 - 4785

Published: Aug. 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.

Language: Английский

Citations

0