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

Research output: Contribution to journal › Article › peer-review

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.

Original language	English
Pages (from-to)	3679-3682
Number of pages	4
Journal	Tetrahedron Letters
Volume	56
Issue number	23
DOIs	https://doi.org/10.1016/j.tetlet.2015.04.063
Publication status	Published - 25 May 2015
Externally published	Yes

Keywords

Cyclobutanones
Cyclopentanones
Radical addition
Ring expansion
Xanthates

Access to Document

10.1016/j.tetlet.2015.04.063

Cite this

@article{f66f8ff27d534f2a81d0773787a81156,

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,

day = "25",

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

language = "English",

volume = "56",

pages = "3679--3682",

journal = "Tetrahedron Letters",

issn = "0040-4039",

number = "23",

}

TY - JOUR

T1 - A flexible route to substituted hydroxy-cyclopentanones from cyclobutanones

AU - Heng, Rama

AU - Zard, Samir Z.

PY - 2015/5/25

Y1 - 2015/5/25

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

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

Abstract

Keywords

Access to Document

Fingerprint

Cite this