The Journal of Organic Chemistry

Samarium (II) iodide-induced reductive cyclization of unactivated olefinic ketones. Sequential radical cyclization/intermolecular nucleophilic addition and substitution …

GA Molander, JA McKie

Index: Molander, Gary A.; McKie, Jeffrey A. Journal of Organic Chemistry, 1992 , vol. 57, # 11 p. 3132 - 3139

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Citation Number: 191

Abstract

Samarium (II) iodide in the presence of HMPA effectively promotee the intramolecular coupling of unactivatad olefinic ketones by a reductive ketyl-oleh radical-cyclization process. The reaction is quite general for the formation of 5 and Smembered carbocycles and even provides modest yields in leas facile cyclization processee a~ evidenced by the generation of methylcyclooctanol via an sendo cyclization. Sequential radical cyclization- ...