Cyclisation d'oximes β-alleniques. Synthese de dihydro-4,7 oxazepines-1,2

Grimaldi, J.; Cormons, A.

doi:10.1016/s0040-4039(00)61938-x

Cited by 24 publications

(8 citation statements)

References 16 publications

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“…This substituent effect also seems to be responsible for the 7-endo cyclization of allenic derivatives, using silver tetrafluoroborate, instead of the more obvious 6-exo cyclization. 25 In the same way a 7-endo cyclization was observed for the reaction of a highly sensitive phenol with phenylselenochloride 26 (Scheme 19).…”

Section: Formation Of Cyclic Ethers By Endo-mode Cyclizationmentioning

confidence: 58%

Preparation of seven and larger membered heterocycles by electrophilic heteroatom cyclization

Rousseau¹,

Homsi²

1997

Chem. Soc. Rev.

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Section: Formation Of Cyclic Ethers By Endo-mode Cyclizationmentioning

confidence: 58%

Preparation of seven and larger membered heterocycles by electrophilic heteroatom cyclization

Rousseau¹,

Homsi²

1997

Chem. Soc. Rev.

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“…Seven-membered rings can also be obtained, as demonstrated by Grimaldi and Cormons, although in peculiar cases. 97 Indeed, these authors described the cyclization of β-allenic oximes to dihydro-4,7-oxazepines in good yields in the presence of silver tetrafluoroborate (Scheme 51). In this reaction, the hydroxyl of the oxime group attacked again the terminal double bond of the allenic system upon silver activation in a 7-endotrig process.…”

Section: Cyclization Of Allenolsmentioning

confidence: 99%

Ag-Mediated Reactions: Coupling and Heterocyclization Reactions

2008

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“…Although seven-membered rings are normally more challenging to obtain, silver-promoted 7-endo cyclisation of b-allenic oximes through the oxygen, has also been reported to give 4,7-dihydro-1,2oxazepines (Scheme 33). 37…”

Section: Intramolecular Addition Of O-hmentioning

confidence: 99%

Silver and platinum-catalysed addition of O–H and N–H bonds to allenes

Muñoz¹

2014

Chem. Soc. Rev.

189

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5Transition-metal catalysed nucleophile addition to allenes is a very powerful tool for the synthesis of functionalised molecules containing heteroatoms, heterocycles in the intramolecular version, or allyl derivatives in the intermolecular. The reaction has been explored with a wide variety of metals, being silver one of the most effective. Although platinum has somehow been less explored, different reactivity has been observed with this metal, showing the great potential and versatility of this methodology. This 10 review will highlight the reactions with these two metals, silver and platinum, when oxygen or nitrogen nucleophiles are employed. Although most of the examples describe the intramolecular version, some intermolecular reactions have been described with platinum, and will also be covered.

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Cyclisation d'oximes β-alleniques. Synthese de dihydro-4,7 oxazepines-1,2

Cited by 24 publications

References 16 publications

Preparation of seven and larger membered heterocycles by electrophilic heteroatom cyclization

Preparation of seven and larger membered heterocycles by electrophilic heteroatom cyclization

Ag-Mediated Reactions: Coupling and Heterocyclization Reactions

Silver and platinum-catalysed addition of O–H and N–H bonds to allenes

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