TY - JOUR
T1 - Observations Regarding the Regiochemical and Stereochemical Course of the Cyclization of Complex 5-Hexenyl Radicals
T2 - An Approach to Perhydronaphthalenes
AU - Chuang, Che-Ping
AU - Gallucci, Judith C.
AU - Hart, David J.
AU - Hoffman, Christopher
PY - 1988/6/1
Y1 - 1988/6/1
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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U2 - 10.1021/jo00249a015
DO - 10.1021/jo00249a015
M3 - Article
AN - SCOPUS:33845279078
SN - 0022-3263
VL - 53
SP - 3218
EP - 3226
JO - Journal of Organic Chemistry
JF - Journal of Organic Chemistry
IS - 14
ER -