Highly efficient, facile, room temperature intermolecular [5 + 2] cycloadditions catalyzed by cationic rhodium(I): one step to cycloheptenes and their libraries.
A cationic rhodium(I) complex--[(C(10)H(8))Rh(cod)](+) SbF(6)(-)--catalyzes the remarkably efficient intermolecular [5 + 2] cycloaddition of vinylcyclopropanes (VCPs) and various alkynes, providing cycloheptene cycloadducts in excellent yields in minutes at room temperature. The efficacy and selectivity of this catalyst are also shown in a novel diversification strategy, affording a cycloadduct library in one step from nine commercially available components.
Wender
Paul A
PA
Department of Chemistry, Stanford University, Stanford, California 94305-5080, USA. wenderp@stanford.edu
Sirois
Lauren E
LE
Stemmler
René T
RT
Williams
Travis J
TJ
D002384:Catalysis; D002412:Cations / Q000737:chemistry; D003500:Cyclization; D003508:Cycloheptanes / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D009942:Organometallic Compounds / Q000737:chemistry*; D012238:Rhodium / Q000737:chemistry*; D054852:Small Molecule Libraries; D013237:Stereoisomerism; D013696:Temperature
D002412:Cations; D003508:Cycloheptanes; D009942:Organometallic Compounds; D054852:Small Molecule Libraries; D012238:Rhodium