2018
DOI: 10.1002/chem.201801062
|View full text |Cite
|
Sign up to set email alerts
|

Catalytic [1,3] O‐to‐C Rearrangement: Rapid Access to Bridged Bicyclic Systems

Abstract: A catalytic [1,3] O-to-C rearrangement from enyne-ethers was developed for the rapid synthesis of diverse bridged bicyclic systems. In this reaction, a vinyl oxonium intermediate, generated in situ from enyne-ether, was the precursor for the [1,3] O-to-C rearrangement. This versatile protocol represents the first example of catalytic [1,3] O-to-C rearrangement based on ring-expansion strategy, enabling efficient access to bridged bicyclic scaffolds.

Help me understand this report

Search citation statements

Order By: Relevance

Paper Sections

Select...
2
1

Citation Types

1
7
0

Year Published

2019
2019
2021
2021

Publication Types

Select...
7

Relationship

1
6

Authors

Journals

citations
Cited by 21 publications
(8 citation statements)
references
References 63 publications
1
7
0
Order By: Relevance
“…Subsequent 3,3‐rearrangement afforded the oxonium intermediate III , with an sp 2 ‐carbon center of the bridgehead atom and a trans ‐double bond. Such unique intermediate was also observed in our previous work . Unlike small‐size cycles, the nine‐membered ring might significantly reduce the ring strain of the intermediate III .…”
Section: Methodssupporting
confidence: 83%
See 3 more Smart Citations
“…Subsequent 3,3‐rearrangement afforded the oxonium intermediate III , with an sp 2 ‐carbon center of the bridgehead atom and a trans ‐double bond. Such unique intermediate was also observed in our previous work . Unlike small‐size cycles, the nine‐membered ring might significantly reduce the ring strain of the intermediate III .…”
Section: Methodssupporting
confidence: 83%
“…We have recently developed a general strategy for efficient construction of bridged oxa‐[4.2.1] skeletons via a gold‐catalyzed [1,3]‐O‐to‐C rearrangement from enyne‐ether . In this reaction, a vinyl oxonium intermediate A , generated in situ from enyne‐ether, was the precursor for the [1,3] O‐to‐C rearrangement (Scheme a).…”
Section: Methodsmentioning
confidence: 99%
See 2 more Smart Citations
“…The authors reasoned that an initial vinyl ether addition onto the activated-alkyne toward the 104 motif might be favored rather than an oxygen attack, as in the previous transformations, mostly due to the strong σ-donor and weak π-acceptor nature of the SIPr ligated gold center (Luo et al, 2018). If the lactone motif is replaced by a tetrahydrofuran group as in compound 106 , then the bicyclo 107 is obtained via a gold(I)-catalyzed 5-exo-dig /[1,3] O-to-C tandem process in a diastereoselective fashion (Figure 10C) (Zhang et al, 2018a). With this set of papers Zhu et al demonstrated the versatility of diverse gold(I) complexes in the ring-expansion process of lactones and related structural motifs via a nucleophilic attack onto an activated alkyne group.…”
Section: Gold-catalyzed Isomerization Processes Involving An Initimentioning
confidence: 99%