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Synfacts 2009(7): 0746-0746  
DOI: 10.1055/s-0029-1217286
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart ˙ New York

Iridium-Salen-Catalyzed Synthesis of Spirocyclopropyl Lactones

Contributor(s): Hisashi Yamamoto, Joshua P. Abell
M. Ichinose, H. Suematsu, T. Katsuki*
Kyushu University, Fukuoka, Japan
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Publication History

Publication Date:
22 June 2009 (online)

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Significance

There are several known methods for the construction of chiral 1,4-cylcoheptadienes. Of the reported methods only low to ­moderate yields and moderate enantioselectivities were observed. In this report Katsuki has expanded on his previous findings of iridium-salen-catalyzed cyclopropanation to furnish α-spirocyclopropyl lactones, which were later derivatized via a Cope rearrangement to give chiral 1,4-cycloheptadienes.