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Synfacts 2010(9): 1000-1000  
DOI: 10.1055/s-0030-1258012
Synthesis of Heterocycles
© Georg Thieme Verlag Stuttgart ˙ New York

Catalytic Hypervalent Iodine Spirolacton-ization Using m-CPBA as Co-Oxidant

Contributor(s): Victor Snieckus, Matthew O. Kitching
M. Uyanik, T. Yasui, K. Ishihara*
Nagoya University, Japan
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Publication History

Publication Date:
23 August 2010 (online)

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Significance

The development and implementation of an enantioselective catalytic oxidative spirolactonization is reported. The synthesis and screening of a number of flexible iodine precatalysts is described (leading to catalyst A as optimal) and the substrate scope is established (see ­Table). Subsequent derivatization to give the ­epoxyspirolactone was achieved through the use of an excess of the co-oxidant (m-CPBA, 5 equiv).