Palladium-catalyzed regioselective cyclopropanating allenylation of (2,3-butadienyl)malonates with propargylic carbonates and their application to synthesize cyclopentenones.
An efficient and highly regioselective route to synthesize polysubstituted 1,3,4-alkatrien-2-yl cyclopropane derivatives via Pd(0)-catalyzed highly regioselective coupling cyclization of (2,3-butadienyl)malonate or bis(phenylsulfonyl)methane with propargylic carbonates was reported. The reaction proceeded smoothly under neutral conditions to afford the products in 73-96% yields. The products may be efficiently converted to cyclopentenone derivatives via a catalytic Pauson-Khand reaction under ambient conditions.
Shu
Wei
W
State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 354 Fenglin Lu, Shanghai 200032, PR China.
Jia
Guochen
G
Ma
Shengming
S
D000480:Alkynes / Q000737:chemistry*; D002254:Carbonates / Q000737:chemistry*; D002384:Catalysis; D003500:Cyclization; D003517:Cyclopentanes / Q000138:chemical synthesis* / Q000737:chemistry; D003521:Cyclopropanes / Q000737:chemistry*; D008314:Malonates / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D009942:Organometallic Compounds / Q000737:chemistry; D010165:Palladium / Q000737:chemistry*; D020005:Propanols / Q000737:chemistry; D013237:Stereoisomerism
D000480:Alkynes; D002254:Carbonates; D003517:Cyclopentanes; D003521:Cyclopropanes; D008314:Malonates; D009942:Organometallic Compounds; D020005:Propanols; D010165:Palladium; C013905:cyclopentenone