2009
DOI: 10.1021/ol901722q
|View full text |Cite
|
Sign up to set email alerts
|

Gold-Catalyzed Synthesis of Carbon-Bridged Medium-Sized Rings

Abstract: Bicyclo[m.n.1]alkenone frameworks possessing quaternary carbon centers adjacent to a bridged ketone are frequently found in bioactive natural products. Although several methods have been developed to construct such frameworks, most of them are specific to a particular scaffold. Herein, we report a mild and highly efficient method to generate carbon-bridged frameworks of various sizes using phosphino gold(I) catalysts.

Help me understand this report

Search citation statements

Order By: Relevance

Paper Sections

Select...
2
2

Citation Types

0
27
0

Year Published

2011
2011
2017
2017

Publication Types

Select...
5
4

Relationship

1
8

Authors

Journals

citations
Cited by 102 publications
(27 citation statements)
references
References 34 publications
0
27
0
Order By: Relevance
“…[23] Typically,t reatment of silyl enol ether 5a with 5mol %o fE chavarren's catalysti nt oluenea t5 08Cf or 17 hours gave the predominant 6-endo-dig cyclization product 6a in excellent yield and stereoselectivity. After several attempts, we found that Barriault'sc onditions gave the optimal results.…”
Section: Resultsmentioning
confidence: 99%
See 1 more Smart Citation
“…[23] Typically,t reatment of silyl enol ether 5a with 5mol %o fE chavarren's catalysti nt oluenea t5 08Cf or 17 hours gave the predominant 6-endo-dig cyclization product 6a in excellent yield and stereoselectivity. After several attempts, we found that Barriault'sc onditions gave the optimal results.…”
Section: Resultsmentioning
confidence: 99%
“…To demonstrate the utility of the denitrogenative aza‐[3+2] cycloaddition, Au I ‐catalyzed cyclizations of silyl enol ether 5 were then carried out (Scheme ). After several attempts, we found that Barriault's conditions gave the optimal results . Typically, treatment of silyl enol ether 5 a with 5 mol % of Echavarren's catalyst in toluene at 50 °C for 17 hours gave the predominant 6‐ endo ‐ dig cyclization product 6 a in excellent yield and stereoselectivity .…”
Section: Resultsmentioning
confidence: 99%
“…More recently, Barriault has demonstrated that the C1-C8 bond of hyperforin can be formed via a novel gold catalyzed cyclization union between a silyl enol ether and an alkyne. 67 …”
Section: Introductionmentioning
confidence: 99%
“…In 2009, we reported a mild and highly efficient method to generate carbon-bridged frameworks of various sizes through a gold(I)-catalyzed carbocyclization [13]. Although the cyclization of enol ether 5 can produce 5- exo and 6- endo products, we found that gold complexes 6 , having bulky phosphine ligands such as 2-bis( tert -butylphosphino)biphenyl, gave exclusively the 6- endo-dig cyclized products 7 (Scheme 1).…”
Section: Introductionmentioning
confidence: 99%