2017
DOI: 10.1002/chem.201700600
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Gold(I)‐Catalyzed Cycloisomerization of ortho‐(Propargyloxy)arenemethylenecyclopropanes Controlled by Adjacent Substituents at Aromatic Rings

Abstract: Gold(I)-catalyzed cycloisomerization of ortho-(propargyloxy)arenemethylenecyclopropanes afforded two different types of products, that is, products of methylenecyclopropane migration and cycloisomerization products of the methylenecyclopropane moiety, controlled jointly by electronic and steric effects of the adjacent substituents. Furthermore, the corresponding cycloisomerization products could be also produced in an enantiomerically enriched manner.

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Cited by 19 publications
(21 citation statements)
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“…Treatment of sabinol 1 with m -CPBA did not yield the desired epoxide 15 . Rather, the generated epoxide underwent an in situ ring-opening process after the electrophilic attack of the formed m -chlorobenzoic acid, resulting in ester 17 ( Scheme 5 ) [ 44 , 45 , 46 ]. The intermediate epoxide could not be isolated even after applying miscellaneous conditions, such as varying temperature, NaHCO 3 or Na 2 CO 3 , or buffer solutions.…”
Section: Resultsmentioning
confidence: 99%
“…Treatment of sabinol 1 with m -CPBA did not yield the desired epoxide 15 . Rather, the generated epoxide underwent an in situ ring-opening process after the electrophilic attack of the formed m -chlorobenzoic acid, resulting in ester 17 ( Scheme 5 ) [ 44 , 45 , 46 ]. The intermediate epoxide could not be isolated even after applying miscellaneous conditions, such as varying temperature, NaHCO 3 or Na 2 CO 3 , or buffer solutions.…”
Section: Resultsmentioning
confidence: 99%
“…Furthermore, we also reported a gold(I)‐catalyzed cycloisomerization of MCP‐containing alkynes 101 , affording two different types of products 104 and 105 , controlled jointly by electronic and steric effects of the adjacent substituents (Scheme a) . The formation of 104 resulted from the higher electron density on the C2 atom when R 1 was a tert ‐butyl ( t Bu) or tert ‐amyl ( t Am) group.…”
Section: Transformations Of Facpsmentioning
confidence: 96%
“…2019, 25,7591 -7606 www.chemeurj.org tronic and steric effects of the adjacent substituents (Scheme 22 a). [28] The formation of 104 resultedf rom the higher electron density on the C2 atom when R 1 was a tertbutyl (tBu) or tert-amyl (tAm) group. Therefore, the alkyne moietyw as firstly activated by the gold catalyst, followed by nucleophilic attack by the aryl ring.…”
Section: Ring-opening Reactions With Proximal Càcb Ond Cleavagementioning
confidence: 99%
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“…Substrates lacking the phenolic ether failed to induce any cyclization reaction (Figure b) . Shi et al further elaborated this approach to assemble chromene and dihydrobenzofuran by introducing the cyclopropane moiety to the olefin …”
Section: Synthesis Of Bio‐relevant Small To Medium Ring‐heterocyclesmentioning
confidence: 99%