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Synlett 1997; 1997(10): 1171-1174
DOI: 10.1055/s-1997-994
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Highly Enantioselective Intermolecular Cyclopropanation Catalyzed by Dirhodium(II) Tetrakis[3(S)-phthalimido-2-piperidinonate]: Solvent Dependency of the Enantioselection

Shinji Kitagaki, Hideo Matsuda, Nobuhide Watanabe, Shun-ichi Hashimoto*
  • *Faculty of Pharmaceutical Sciences, Hokkaido University, Sapporo 060, Japan, Fax +81(11)706-4981; E-mail hsmt@pharm.hokudai.ac.jp
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Publication History

Publication Date:
31 December 2000 (online)

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The enantioselectivity in cyclopropanations catalyzed by dirhodium(II) tetrakis[3(S)-phthalimido-2-piperidinonate] has been found to be substantially improved by employing ether as the rarely used solvent. Cyclopropanations of styrenes or 1,1-disubstituted alkenes with 2,4-dimethyl-3-pentyl diazoacetate in ether are promoted by this catalyst to afford the corresponding cyclopropane products in the highest levels of enantioselectivity (up to 98% ee) reported to date for the dirhodium(II)-catalyzed intermolecular cyclopropanation reactions.

enantioselective cyclopropanation - dirhodium(II) tetrakis[3(S)-phthalimido-2-piperidinonate] - diazoacetate - solvent effect

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