594845-29-1Relevant academic research and scientific papers
Reactions of aldehydes with organozinc reagents derived from (E)-3-bromo- And ( E)-3-iodo-1-phenylsulfonylprop-1-ene
Gallagher, Eva T.,Grayson, David H.
, p. 420 - 429 (2015/02/19)
(E)-3-Bromo-1-phenylsulfonylprop-1-ene and (E)-3-iodo-1-phenylsulfonylprop-1-ene both form allylic organozinc reagents that react with aromatic aldehydes to give mainly 4-aryl-4-hydroxy-1-phenylsulfonylbut-1-enes. In contrast, reactions of the same organo
Reactions of lithiated (E)-3-halo-1-phenylsulfonylprop-1-enes and (Z)-1-halo-3-phenylsulfonylprop-1-enes with aldehydes
Gallagher, Eva T.,Grayson, David H.
, p. 1374 - 1381 (2007/10/03)
(E)-3-Chloro-1-phenylsulfonylprop-1-ene and its iodo- and bromo- analogues, (Z)-1-iodo-3-phenylsulfonylprop-1-ene and (Z)-1-bromo-3-phenylsulfonylprop-1-ene, have each been successfully converted into lithiated carbanions which react regioselectively with aromatic aldehydes to give γ-alkylated products whose nature depends upon the halogen substituent; the chloro-sulfones yield (2Z)-1-aryl-1-chloro-4-phenylsulfonylbut-2-en-1-ols but the bromo- and iodo-derivatives behave differently, yielding (1E)-trans-4-aryl-3,4-epoxy-1-phenylsulfonylbut-1-enes. In sharp contrast, the same lithiated sulfones react with aliphatic aldehydes to give anti-configured β-hydroxysulfones which are formed via diastereoselective α-alkylation reactions.
