Gold‐Catalyzed Cycloisomerization of Yne‐Vinylidenecyclopropanes: A Three‐Carbon Synthon for [3+2] Cycloadditions

Yuan, Wei; Tang, Xiang‐Ying; Wei, Yin; Shi, Min

doi:10.1002/chem.201304579

Cited by 25 publications

(5 citation statements)

References 123 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…In 2014, Shi's group reported a novel intramolecular cycloisomerization of yne-VDCPs substrates 148 and 149 under Au(I) catalysis (Scheme 27). 63 The length of the carbon chain that links the alkynyl group with the VDCP moiety is the key factor to influence the nature of the product obtained from the cycloisomerization reaction. When n = 1, the bicyclic derivatives 150 could be delivered smoothly as the major products under Au(I) activation on the C−C triple bond.…”

Section: Gold-catalyzed Cycloisomerization Reactions Of Vdcpsmentioning

confidence: 99%

Gold-Catalyzed Conversion of Highly Strained Compounds

et al. 2020

Self Cite

View full text Add to dashboard Cite

The past decade has witnessed the golden age of homogeneous gold-catalyzed reactions, especially those that involve the transformation of highly strained molecules into complex molecular architectures. Gold catalysts, with unique electronic properties and catalytic abilities, have elevated versatile reaction modes through π-interaction induced activation. On the basis of increasing research interest in this topic, together with the significant development of various ligands, including phosphine ligands and azacyclic or noncyclic carbene ligands, the understanding of the catalytic function of gold catalysts has become much deeper and more comprehensive. Different reaction needs thus could be adapted by a novel gold catalyst with a diversified ligand selection. Furthermore, the whole evolution of the gold catalysis on synthetic methodologies has realized and expanded its application into natural product synthesis as well as the potentiality of drug discovery, which endows this ancient metal with a magnificent renaissance. The reactivity of strained small ring molecules with high tension has always been an important research topic in organic chemistry. When the highly strained small ring is linked with a π-electron rich moiety or contains a heteroatom, the gold activation of the π-system or coordination with the heteroatom can initiate a cascade reaction, usually followed by ring opening or expansion. These processes can result in the rapid construction of complex and distinct molecular structures, many of which feature in biologically important molecules. In this review, we will mainly summarize the advances on diverse reaction types and molecular constructions accomplished by homogeneous gold catalysis using highly strained substrates, including methylenecyclopropanes (MCPs), vinylidenecyclopropanes (VDCPs), cyclopropenes as well as aziridine- and epoxide-containing molecules, focusing on the last 10 years. For functionalized alkynyl cyclopropanes, several early inspiring and elegant examples will be described in this review for systematically understanding these transformations.

show abstract

Section: Gold-catalyzed Cycloisomerization Reactions Of Vdcpsmentioning

confidence: 99%

Gold-Catalyzed Conversion of Highly Strained Compounds

et al. 2020

Self Cite

View full text Add to dashboard Cite

show abstract

“…Gold catalysts inside self-assembled nanospheres were employed for enyne metathesis and other gold-catalyzed transformations [1194]. A DFT study of gold catalyzed cycloisomerization/enyne metathesis using yne-vinylidenecyclopropanes suggested that alkylidenecyclopropylcarbene complexes were likely not intermediates due to the high energy of these species [1195]. .…”

Section: )mentioning

confidence: 99%

The chemistry of the carbon-transition metal double and triple bond: Annual survey covering the year 2014

Herndon

2016

Coordination Chemistry Reviews

View full text Add to dashboard Cite

“…A 6‐ or 7‐ exo ‐dig cyclization in alleneynes ( 59 ) led to a tertiary carbocation intermediate ( 63 ), which was attacked by the vinyl gold to form a final bicyclotriene ( 60 ) or a dihydropyrrole allene ( 61 ) as major product respectively. Formation of 61 plausibly follows the 7‐ exo ‐dig cyclization of allenyne to result into a formal [2+2] cycloaddition product 67 that undergoes further skeleton rearrangement to yield allene ( 61 , Figure ) …”

Section: Synthesis Of Bio‐relevant Small To Medium Ring‐heterocyclesmentioning

confidence: 99%

Gold(I) Catalyzed Enyne Cycloisomerization – A Roadmap to Privileged Heterocyclic Scaffolds

Lee

Kumar

2018

Israel Journal of Chemistry

View full text Add to dashboard Cite

Gold(I) catalyzed cycloisomerization reaction is one of the key transformations that remain underexplored to build molecular diversity and complexity. In this review, we summarize synthesis endeavors where enyne cycloisomerization chemistry was utilized to form structurally intriguing as well as biologically relevant heterocyclic scaffolds. To this goal, most of the efforts tend to exploit gold carbene type intermediates, often supporting a cyclopropane ring and transform them into new scaffolds. Various examples have been grouped together to highlight the role of presence or absence of external heteroatom nucleophiles in modulating reactive intermediates into novel molecular frameworks. The last section is devoted to the emerging role of gold(I) catalyzed cycloisomerization reactions in driving the divergent synthesis approaches wherein a common substrate can be transformed into distinct molecular scaffolds by merely varying reaction conditions or gold complexes.

show abstract

Gold‐Catalyzed Cycloisomerization of Yne‐Vinylidenecyclopropanes: A Three‐Carbon Synthon for [3+2] Cycloadditions

Cited by 25 publications

References 123 publications

Gold-Catalyzed Conversion of Highly Strained Compounds

Gold-Catalyzed Conversion of Highly Strained Compounds

The chemistry of the carbon-transition metal double and triple bond: Annual survey covering the year 2014

Gold(I) Catalyzed Enyne Cycloisomerization – A Roadmap to Privileged Heterocyclic Scaffolds

Contact Info

Product

Resources

About