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Synfacts 2008(1): 0046-0046  
DOI: 10.1055/s-2007-991432
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart · New York

Reverse-Electron-Demand Cycloaddition of Carbonyl Ylides

Contributor(s): Hisashi Yamamoto, Joshua N. Payette
H. Suga*, D. Ishimoto, S. Higuchi, M. Ohtsuka, T. Arikawa, T. Tsuchida, A. Kakehi, T. Baba
Shinshu University, Nagano and Tokyo Institute of Technology, Yokohama, Japan
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Publication History

Publication Date:
18 December 2007 (online)

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Significance

Compared to previous reports by Hodgson and Hashimoto (e.g., J. Am. Chem. Soc. 1999, 121, 1417), the authors report a conceptually new enantioselective dipole-HOMO/dipolarophile-LUMO-controlled cycloaddition of carbonyl ylides. The use of a chiral Ni-binaphthyldiimine complex in combination with bulky vinyl ethers gave the epoxy-bridged endo adducts in good to excellent yields and enantioselectivities. Use of several lanthanoid metals with pybox-type ligands also provided access to related polycyclic structures.