Thermal, three-carbon + two-atom cycloaddition of cyclopropenone ketals with carbon-heteroatom double bonds: Butenolide, furan, and γ-keto ester preparation.

Dale L. Boger; Christine E. Brotherton; Gunda I. Georg

doi:10.1016/S0040-4039(01)91394-2

Thermal, three-carbon + two-atom cycloaddition of cyclopropenone ketals with carbon-heteroatom double bonds: Butenolide, furan, and γ-keto ester preparation.

Dale L. Boger, Christine E. Brotherton, Gunda I. Georg

Medicinal Chemistry

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Abstract

A preliminary study of the thermal reaction of cyclopropenone ketals with carbon-heteroatom double bonds is detailed. The reaction with aldehyde and keto carbonyls provide butenolide ortho esters, the product of a formal three-carbon + two-atom cycloaddition of the cyclopropenone ketal across the carbon-oxygen double bond.

Original language	English (US)
Pages (from-to)	5615-5618
Number of pages	4
Journal	Tetrahedron Letters
Volume	25
Issue number	49
DOIs	https://doi.org/10.1016/S0040-4039(01)91394-2
State	Published - 1984

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title = "Thermal, three-carbon + two-atom cycloaddition of cyclopropenone ketals with carbon-heteroatom double bonds: Butenolide, furan, and γ-keto ester preparation.",

abstract = "A preliminary study of the thermal reaction of cyclopropenone ketals with carbon-heteroatom double bonds is detailed. The reaction with aldehyde and keto carbonyls provide butenolide ortho esters, the product of a formal three-carbon + two-atom cycloaddition of the cyclopropenone ketal across the carbon-oxygen double bond.",

author = "Boger, {Dale L.} and Brotherton, {Christine E.} and Georg, {Gunda I.}",

year = "1984",

doi = "10.1016/S0040-4039(01)91394-2",

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volume = "25",

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journal = "Tetrahedron Letters",

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number = "49",

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T1 - Thermal, three-carbon + two-atom cycloaddition of cyclopropenone ketals with carbon-heteroatom double bonds

T2 - Butenolide, furan, and γ-keto ester preparation.

AU - Boger, Dale L.

AU - Brotherton, Christine E.

AU - Georg, Gunda I.

PY - 1984

Y1 - 1984

N2 - A preliminary study of the thermal reaction of cyclopropenone ketals with carbon-heteroatom double bonds is detailed. The reaction with aldehyde and keto carbonyls provide butenolide ortho esters, the product of a formal three-carbon + two-atom cycloaddition of the cyclopropenone ketal across the carbon-oxygen double bond.

AB - A preliminary study of the thermal reaction of cyclopropenone ketals with carbon-heteroatom double bonds is detailed. The reaction with aldehyde and keto carbonyls provide butenolide ortho esters, the product of a formal three-carbon + two-atom cycloaddition of the cyclopropenone ketal across the carbon-oxygen double bond.

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U2 - 10.1016/S0040-4039(01)91394-2

DO - 10.1016/S0040-4039(01)91394-2

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VL - 25

SP - 5615

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JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 49

ER -

Thermal, three-carbon + two-atom cycloaddition of cyclopropenone ketals with carbon-heteroatom double bonds: Butenolide, furan, and γ-keto ester preparation.

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