Rh(I)-catalyzed carbonylative ring opening of diazabicycles with acyl anion equivalents.
A catalytic desymmetrization of strained alkenes by ring-opening of meso-diazabicycles with acyl anion nucleophiles is reported. Densely functionalized trans-1,2-hydrazinoacyl cyclopentene building blocks are obtained stereoselectively. The acyl anion equivalent is generated in situ under very mild conditions from readily available organoboron precursors.
Menard
Frederic
F
Davenport Research Laboratories, University of Toronto, 80 St. George Street, Toronto, Ontario, Canada M5S 3H6.
Weise
Christian Frederik
CF
Lautens
Mark
M
D000838:Anions; D053961:Azabicyclo Compounds / Q000737:chemistry*; D002384:Catalysis; D007659:Ketones / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy; D012211:Rhenium / Q000737:chemistry*
D000838:Anions; D053961:Azabicyclo Compounds; D007659:Ketones; D012211:Rhenium