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Paper | Special issue | Vol 88, No. 1, 2014, pp.245-260
Published online, 28th May, 2013
DOI: 10.3987/COM-13-S(S)11
Efficient Oxidative Spirolactamization by μ-Oxo Bridged Heterocyclic Hypervalent Iodine Compound

Toshifumi Dohi, Eisuke Mochizuki, Daisuke Yamashita, Keitaro Miyazaki, and Yasuyuki Kita*

*College of Pharmaceutical Sciences, Ritsumeikan University, 1-1-1 Nojihigashi, Kusatsu, Shiga, 525-8577, Japan

Abstract

In this report, the authors have clarified that the μ-oxo bridged heterocyclic hypervalent iodine compound 1 shows a more effective reactivity in the oxidative dearomatizing spirolactamization compared to conventional PIDA (phenyliodine(III) diacetate). Besides the high reactivity, a new selectivity during the oxidations based on the steric discrimination of the nitrogen groups of the pre-spirocyclic substrates is demonstrated for the heterocyclic hypervalent iodine compound 1.