Observations Regarding the Regiochemical and Stereochemical Course of the Cyclization of Complex 5-Hexenyl Radicals: An Approach to Perhydronaphthalenes

Che Ping Chuang; Judith C. Gallucci; David J. Hart; Christopher Hoffman

doi:10.1021/jo00249a015

Observations Regarding the Regiochemical and Stereochemical Course of the Cyclization of Complex 5-Hexenyl Radicals: An Approach to Perhydronaphthalenes

Che Ping Chuang, Judith C. Gallucci, David J. Hart, Christopher Hoffman

Department of Chemistry

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

26 Citations (Scopus)

Abstract

Iodo lactones 4 and 5 were prepared from m-anisic acid (10) and m-(isopropylthio)benzoic acid (15),respectively, by using a reductive alkylation-halolactonization-free radical cyclization sequence. Enones 6-9 were prepared from benzoic acid by way of acid chloride 30 by using a palladium-catalyzed coupling reaction. Tri-n-butyltin hydride mediated cyclization of 4-7 and 9 afforded substituted perhydronaphthalenes with good stereoselectivity. The radical derived from enone 8 gave perhydroindan 40. A transition-state geometry for the cyclization of enones 6-9 is proposed.

Original language	English
Pages (from-to)	3218-3226
Number of pages	9
Journal	Journal of Organic Chemistry
Volume	53
Issue number	14
DOIs	https://doi.org/10.1021/jo00249a015
Publication status	Published - 1988 Jun 1

All Science Journal Classification (ASJC) codes

Organic Chemistry

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10.1021/jo00249a015

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abstract = "Iodo lactones 4 and 5 were prepared from m-anisic acid (10) and m-(isopropylthio)benzoic acid (15),respectively, by using a reductive alkylation-halolactonization-free radical cyclization sequence. Enones 6-9 were prepared from benzoic acid by way of acid chloride 30 by using a palladium-catalyzed coupling reaction. Tri-n-butyltin hydride mediated cyclization of 4-7 and 9 afforded substituted perhydronaphthalenes with good stereoselectivity. The radical derived from enone 8 gave perhydroindan 40. A transition-state geometry for the cyclization of enones 6-9 is proposed.",

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T1 - Observations Regarding the Regiochemical and Stereochemical Course of the Cyclization of Complex 5-Hexenyl Radicals

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AU - Chuang, Che Ping

AU - Gallucci, Judith C.

AU - Hart, David J.

AU - Hoffman, Christopher

PY - 1988/6/1

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N2 - Iodo lactones 4 and 5 were prepared from m-anisic acid (10) and m-(isopropylthio)benzoic acid (15),respectively, by using a reductive alkylation-halolactonization-free radical cyclization sequence. Enones 6-9 were prepared from benzoic acid by way of acid chloride 30 by using a palladium-catalyzed coupling reaction. Tri-n-butyltin hydride mediated cyclization of 4-7 and 9 afforded substituted perhydronaphthalenes with good stereoselectivity. The radical derived from enone 8 gave perhydroindan 40. A transition-state geometry for the cyclization of enones 6-9 is proposed.

AB - Iodo lactones 4 and 5 were prepared from m-anisic acid (10) and m-(isopropylthio)benzoic acid (15),respectively, by using a reductive alkylation-halolactonization-free radical cyclization sequence. Enones 6-9 were prepared from benzoic acid by way of acid chloride 30 by using a palladium-catalyzed coupling reaction. Tri-n-butyltin hydride mediated cyclization of 4-7 and 9 afforded substituted perhydronaphthalenes with good stereoselectivity. The radical derived from enone 8 gave perhydroindan 40. A transition-state geometry for the cyclization of enones 6-9 is proposed.

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Observations Regarding the Regiochemical and Stereochemical Course of the Cyclization of Complex 5-Hexenyl Radicals: An Approach to Perhydronaphthalenes

Abstract

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