A facile synthesis of bicyclo [mn 1] alkan-1-ols. Evidence for organosamarium intermediates in the samarium (II) iodide promoted intramolecular Barbier-type reaction

GA Molander, JA McKie

Index: Molander, Gary A.; McKie, Jeffrey A. Journal of Organic Chemistry, 1991 , vol. 56, # 13 p. 4112 - 4120

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Citation Number: 149

Abstract

Samarium (II) iodide (SmI. j has been succB88fuuy employed as a reductive coupling agent for the intramolecular Barbier-type syntheah of bicyclo [mnl] alkan-l-ola Thus, a variety of%(eiodoeJkyl) cycloakanonea, upon treatment with SmIz and a catalytic quantity of iron complex in tetrahydrofuran (THF), provide the title compounds in excellent yields. The reaction is quite general for the construction of diverse bicyclic ring systems, including the ...