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Synfacts 2010(5): 0602-0602  
DOI: 10.1055/s-0029-1219751
Organo- and Biocatalysis
© Georg Thieme Verlag Stuttgart ˙ New York

Kita’s Oxidative Spirolactonization Catalyzed by a Hypervalent Iodine(III) Species

Contributor(s): Benjamin List, Kristina Zumbansen
M. Uyanik, T. Yasui, K. Ishihara*
Nagoya University and Japan Science and Technology Agency, CREST, Nagoya, Japan
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Publication History

Publication Date:
22 April 2010 (online)

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Significance

Ishihara and co-workers report the rational design of a conformationally flexible C 2-symmetric iodosyl arene catalyst which has been applied in the enantioselective Kita oxidative spirolactonization. Oxidant 2 is formed in situ from catalyst 1 and mCPBA. It is speculated that oxidant 2 has n-σ* or ­hydrogen-bonding interactions between the ­iodine(III) center and the amide side chain. Even a 4-benzoylnaphthol derivative could be synthesized with good enantioselectivity (er = 91:5:8.5), which only gave racemic product using Kita’s method.