Abstract
The diastereoselective ruthenium(II) porphyrin catalyzed cyclopropanation of a variety of alkenes with aryl diazomethanes generated in situ from stable tosylhydrazone derivatives, was achieved in good to excellent yields (up to 92%) and product turnovers. The practical utility of [Ru II( p-Cl-TPP)(CO)] (H 2( p-Cl-TPP)= meso-tetrakis( p-chlorophenyl)porphyrin) 3 was illustrated in the synthesis of the potent HIV-1 reverse transcriptase inhibitor 10 . Preferential formation of sulfone products for reactions involving o- and m-monosubstituted aryl tosylhydrazones demonstrated a hitherto unknown ruthenium(II) porphyrin catalyzed sulfonation reaction.
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