37877-46-6Relevant academic research and scientific papers
Catalyzed hydroboration of allyl sulfonamides
Hamilton, Michael G.,Hughes, Catrin E.,Irving, Alison M.,Vogels, Christopher M.,Westcott, Stephen A.
, p. 143 - 147 (2007/10/03)
The hydroboration of allyl sulfonamides (4-H3CC6 H4SO2NRCH2CH=CH2: R=H, 1; Ph, 2; Bz, 3) with catecholborane (HBcat) using different rhodium catalysts has been examined using multinuclear NMR spectroscopy. Reactions give complex product distributions, regardless of the choice of catalyst, arising from a competing isomerization reaction. This isomerization reaction can be used with N-substituted allyl sulfonamides 2 and 3 to give the corresponding enamines (4-H3 CC6H4SO2CH=CH2 CH3), which in turn react with HBcat to give regioselective formation of one isomer (4-H3CC6H4 SO2NRCH2CH2(Bcat)CH3).
