(R)-l-fluoro-3-[(4-methylpheny@ulfinyl]-2-propanone (1) reacts with diazomethane tiording Q-2- (fluoromethyl)-2-{ [(R)-(4-m&ylphenyl)sul6nyl]methyl}oxirane (2) as the main product. The influence of reaction wnditions (solvent temperature) on the chemo- and stereoselectivity has been studied. Several elaborations of 2, including reactions on the chiral auxiliary and opening of the oxirane ring by carbon nitrogen, oxygen, phosphorus and halogen nucleophiles. are described. Full structural elucidation of the products is provided.
Synthesis of Fluorinated Chirons: Stereoselective Oxirane Formation by Reaction of Diazomethane on 1-Fluoro-3-arylsulfinyl-2-propanone and Ring Opening by Selected Nucleophiles
CRUCIANELLI, MARCELLO
1995-01-01
Abstract
(R)-l-fluoro-3-[(4-methylpheny@ulfinyl]-2-propanone (1) reacts with diazomethane tiording Q-2- (fluoromethyl)-2-{ [(R)-(4-m&ylphenyl)sul6nyl]methyl}oxirane (2) as the main product. The influence of reaction wnditions (solvent temperature) on the chemo- and stereoselectivity has been studied. Several elaborations of 2, including reactions on the chiral auxiliary and opening of the oxirane ring by carbon nitrogen, oxygen, phosphorus and halogen nucleophiles. are described. Full structural elucidation of the products is provided.File in questo prodotto:
Non ci sono file associati a questo prodotto.
Pubblicazioni consigliate
I documenti in IRIS sono protetti da copyright e tutti i diritti sono riservati, salvo diversa indicazione.
