CO2-activation for γ-butyrolactones and its application in the total synthesis of (±)-heteroplexisolide E.
An efficient nickel(0)-catalyzed highly regio- and stereoselective hydrocarboxylation of homopropargylic alcohols with ZnEt(2)  in the presence of CO(2)  (1 atm, balloon) to synthesize α-alkylidene-γ-butyrolactones is described. The catalyst is highly active and can be applied for the synthesis of (optically active) mono- or bicyclic α-alkylidene-γ-butyrolactones with excellent regio- and stereoselectivity and good functional group tolerance. The potential of the reaction has been demonstrated in the first synthesis of (±)-heteroplexisolide E.
State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Lu, Shanghai 200032, P. R. China.
Suhua
S
Li
Shengming
S
Ma
D015107:4-Butyrolactone / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry*; D002245:Carbon Dioxide / Q000737:chemistry*; D002384:Catalysis; D009532:Nickel / Q000737:chemistry; D013237:Stereoisomerism
D002245:Carbon Dioxide; D009532:Nickel; D015107:4-Butyrolactone