Gold(<scp>i</scp>)-catalyzed diastereo- and enantioselective [4 + 3] cycloadditions: construction of functionalized furano-benzoxepins

Wang, Xunhua; Lv, Ruifeng; Li, Xiaoxun

doi:10.1039/d2qo01070d

Cited by 6 publications

(1 citation statement)

References 65 publications

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“…1B ) 75 – 92 . Elegant catalytic systems and different cyclization reactions were successfully developed by the groups of Zhang, Ma, Chi, Zhou, Liu, Deng and others 93 – 100 . For instance, the Chi group reported the synthesis of furan-fused lactams via cycloisomerization/(4 + 2) cycloadditions by gold/NHC relay catalysis 93 .…”

Section: Introductionmentioning

confidence: 99%

Silver/chiral pyrrolidinopyridine relay catalytic cycloisomerization/(2 + 3) cycloadditions of enynamides to asymmetrically synthesize bispirocyclopentenes as PDE1B inhibitors

Jiang

Zhang

et al. 2023

Commun Chem

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Significant progress has been made in asymmetric synthesis through the use of transition metal catalysts combined with Lewis bases. However, the use of a dual catalytic system involving 4-aminopyridine and transition metal has received little attention. Here we show a metal/Lewis base relay catalytic system featuring silver acetate and a modified chiral pyrrolidinopyridine (PPY). It was successfully applied in the cycloisomerization/(2 + 3) cycloaddition reaction of enynamides. Bispirocyclopentene pyrazolone products could be efficiently synthesized in a stereoselective and economical manner (up to >19:1 dr, 99.5:0.5 er). Transformations of the product could access stereodivergent diastereoisomers and densely functionalized polycyclic derivatives. Mechanistic studies illustrated the relay catalytic model and the origin of the uncommon chemoselectivity. In subsequent bioassays, the products containing a privileged drug-like scaffold exhibited isoform-selective phosphodiesterase 1 (PDE1) inhibitory activity in vitro. The optimal lead compound displayed a good therapeutic effect for ameliorating pulmonary fibrosis via inhibiting PDE1 in vivo.

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Section: Introductionmentioning

confidence: 99%

Silver/chiral pyrrolidinopyridine relay catalytic cycloisomerization/(2 + 3) cycloadditions of enynamides to asymmetrically synthesize bispirocyclopentenes as PDE1B inhibitors

Jiang

Zhang

et al. 2023

Commun Chem

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Silver‐catalyzed Cascade Bis‐heteroannulation Reaction of Enynones and o‐Hydroxyphenyl Enaminones: Access to Highly Functionalized 3‐Furylmethyl Chromones

Zhang,

Liu,

Qiu

et al. 2024

Adv Synth Catal

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A general and efficient synthetic protocol was developed to synthesize highly functionalized 3‐furylmethyl chromones from enynones and o‐hydroxyphenyl enaminones via silver‐catalyzed cascade bis‐heteroannulation reaction. This strategy features broad substrate scope broad and good functional group tolerance. Furthermore, the 3‐furylmethyl chromone skeleton shows the potential synthetic application value through further gram‐scale synthesis and derivatization.

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Recent Progress in Transformations of Yne‐enones

Doraghi,

Aghanour Ashtiani,

Dastyafteh

et al. 2024

Adv Synth Catal

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Due to the presence of multiple reactive sites, including an alkyne, an alkene, and a ketone, 2‐(1‐alkynyl)‐2‐alken‐1‐ones (yne‐enones) can successfully participate in the synthesis of various carbo‐, and heterocycles, as well as acyclic compounds. In this regard, a wide variety of transition metal catalysts and organocatalysts are utilized in cycloaddition and functionalization reactions of yne‐enones with other coupling partners. Considering the versatility of this synthon, in this review, we have described metal‐catalyzed and non‐metal‐catalyzed transformations of yne‐enones over the last decade.

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Gold(i)-catalyzed diastereo- and enantioselective [4 + 3] cycloadditions: construction of functionalized furano-benzoxepins

Abstract: Enantioselective higher-order cycloaddition involving gold-furyl 1,3-dipoles is an attractive but challenging transformation for the construction of chiral polycyclic medium-sized rings from readily available building blocks. Here, the gold-catalyzed asymmetric [4+3]...

Cited by 6 publications

References 65 publications

Silver/chiral pyrrolidinopyridine relay catalytic cycloisomerization/(2 + 3) cycloadditions of enynamides to asymmetrically synthesize bispirocyclopentenes as PDE1B inhibitors

Silver/chiral pyrrolidinopyridine relay catalytic cycloisomerization/(2 + 3) cycloadditions of enynamides to asymmetrically synthesize bispirocyclopentenes as PDE1B inhibitors

Silver‐catalyzed Cascade Bis‐heteroannulation Reaction of Enynones and o‐Hydroxyphenyl Enaminones: Access to Highly Functionalized 3‐Furylmethyl Chromones

Recent Progress in Transformations of Yne‐enones

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