111. Catalytic Asymmetric Cyclopropanation of Heteroaryldiazoacetates

Authors: Huw M. L. Davies and Robert J. Townsend

J. Org. Chem.,

2001, 66 (20), 6595–6603


Rh2(S-DOSP)4-catalyzed decomposition of heteroaryldiazoacetates in the presence of styrene results in highly diastereoselective and enantioselective cyclopropanations. Heteroaryldiazoacetates containing both electron-rich and electron-deficient heterocycles, such as thiophene, furan, pyridine, indole, oxazole, isoxazole, and benzoxazole, are effective in this chemistry. These studies broaden the range of diazo compounds containing both electron-withdrawing and electron-donating groups, which undergo highly diastereoselective cyclopropanations.

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