Rh-2(S-DOSP)(4)-catalyzed decomposition of heteroaryldiazoacetates in the p
resence of styrene results in highly diastereoselective and enantioselectiv
e cyclopropanations. Heteroaryldiazoacetates containing both electron-rich
and electron-deficient heterocycles, such as thiophene, furan, pyridine, in
dole, oxazole, isoxazole, and benzoxazole, are effective in this chemistry.
These studies broaden the range of diazo compounds containing both electro
n-withdrawing and electron-donating groups, which undergo highly diastereos
elective cyclopropanations.