Catalytic asymmetric cyclopropanation of heteroaryldiazoacetates.
Rh(2)(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.
Davies
H M
HM
Department of Chemistry, State University of New York at Buffalo, 14260-3000, USA. hdavies@acsu.buffalo.edu
Townsend
R J
RJ
D002384:Catalysis; D003521:Cyclopropanes / Q000737:chemistry*; D003979:Diazonium Compounds / Q000737:chemistry*; D006571:Heterocyclic Compounds / Q000737:chemistry; D013237:Stereoisomerism
D003521:Cyclopropanes; D003979:Diazonium Compounds; D006571:Heterocyclic Compounds; C032111:diazoacetic ester