Highly regio- and chemoselective ring opening of oxa-bridged piperidinones toward functionalized furanones and piperidines.
Lewis acid mediated competitive ring-opening reactions of N-tosyl-substituted oxa-bridged piperidinone ring systems are demonstrated. A majority of the Lewis acids furnished the regio- and chemoselective reductive ring opening at the C(1)-N bond, whereas TiCl(4) furnished at the C(1)-O bond in the presence of triethylsilane, affording functionalized furanones and dihydroxypiperidines, respectively. [reaction: see text]
Muthusamy
Sengodagounder
S
School of Chemistry, Bharathidasan University, Tiruchirappalli, Tamilnadu-620 024, India. muthu@bdu.ac.in
Krishnamurthi
Janagiraman
J
Suresh
Eringathodi
E