A flexible route to substituted hydroxy-cyclopentanones from cyclobutanones

Rama Heng; Samir Z. Zard

doi:10.1016/j.tetlet.2015.04.063

A flexible route to substituted hydroxy-cyclopentanones from cyclobutanones

Rama Heng
, Samir Z. Zard

Laboratoire de Synthèse Organique

Résultats de recherche: Contribution à un journal › Article › Revue par des pairs

Résumé

Acetonyl radicals derived from TBS-protected 1-(α-xanthylacetyl)-1-cyclobutanes readily undergo addition to unactivated alkenes. Deprotection of the resulting adducts with Et₄NF/THF and exposure to silica gel cause ring expansion to give substituted hydroxycyclopentanones. Products of addition to allyl cyanide also underwent β-elimination of the xanthate when treated with Et₄NF/THF.

langue originale	Anglais
Pages (de - à)	3679-3682
Nombre de pages	4
journal	Tetrahedron Letters
Volume	56
Numéro de publication	23
Les DOIs	https://doi.org/10.1016/j.tetlet.2015.04.063
état	Publié - 25 mai 2015
Modification externe	Oui

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10.1016/j.tetlet.2015.04.063

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title = "A flexible route to substituted hydroxy-cyclopentanones from cyclobutanones",

abstract = "Acetonyl radicals derived from TBS-protected 1-(α-xanthylacetyl)-1-cyclobutanes readily undergo addition to unactivated alkenes. Deprotection of the resulting adducts with Et4NF/THF and exposure to silica gel cause ring expansion to give substituted hydroxycyclopentanones. Products of addition to allyl cyanide also underwent β-elimination of the xanthate when treated with Et4NF/THF.",

keywords = "Cyclobutanones, Cyclopentanones, Radical addition, Ring expansion, Xanthates",

author = "Rama Heng and Zard, \{Samir Z.\}",

year = "2015",

month = may,

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doi = "10.1016/j.tetlet.2015.04.063",

language = "English",

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pages = "3679--3682",

journal = "Tetrahedron Letters",

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AU - Heng, Rama

AU - Zard, Samir Z.

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N2 - Acetonyl radicals derived from TBS-protected 1-(α-xanthylacetyl)-1-cyclobutanes readily undergo addition to unactivated alkenes. Deprotection of the resulting adducts with Et4NF/THF and exposure to silica gel cause ring expansion to give substituted hydroxycyclopentanones. Products of addition to allyl cyanide also underwent β-elimination of the xanthate when treated with Et4NF/THF.

AB - Acetonyl radicals derived from TBS-protected 1-(α-xanthylacetyl)-1-cyclobutanes readily undergo addition to unactivated alkenes. Deprotection of the resulting adducts with Et4NF/THF and exposure to silica gel cause ring expansion to give substituted hydroxycyclopentanones. Products of addition to allyl cyanide also underwent β-elimination of the xanthate when treated with Et4NF/THF.

KW - Cyclobutanones

KW - Cyclopentanones

KW - Radical addition

KW - Ring expansion

KW - Xanthates

UR - https://www.scopus.com/pages/publications/84937762077

U2 - 10.1016/j.tetlet.2015.04.063

DO - 10.1016/j.tetlet.2015.04.063

M3 - Article

AN - SCOPUS:84937762077

SN - 0040-4039

VL - 56

SP - 3679

EP - 3682

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 23

ER -

A flexible route to substituted hydroxy-cyclopentanones from cyclobutanones

Résumé

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