Sequenced Reactions with Samarium (II) Iodide. Domino Epoxide Ring-Opening/Ketyl Olefin Coupling Reactions

GA Molander, C del Pozo Losada

Index: Molander, Gary A.; Losada, Carlos Del Pozo Journal of Organic Chemistry, 1997 , vol. 62, # 9 p. 2935 - 2943

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Citation Number: 39

Abstract

A new sequential reductive coupling process promoted by samarium (II) iodide is described. Cascade epoxide ring opening and ketyl radical olefin cyclization leads to a variety of cis-1, 3-cyclopentanediols and cis-1, 3-cyclohexanediols in good yields and with high diastereoselectivity.