Intramolecular iron-mediated diene/olefin cyclocoupling: formation of carbon spirocycles.
[reaction: see text] A short and convenient diastereoselective synthesis of all-carbon spirocylic molecules was developed. A straightforward protocol that involves rearrangement of the diene-Fe(CO)(3) complex followed by cyclization delivers the desired product. The reaction substrates were easily prepared by reaction of an appropriate nucleophile and a cyclohexadienyl-Fe(CO)(3) cation.
Pearson
Anthony J
AJ
Department of Chemistry, Case Western Reserve University, Cleveland, Ohio 44106, USA. ajp4@case.edu
Wang
Xiaolong
X
Dorange
Ismet B
IB
D000475:Alkenes / Q000737:chemistry*; D002384:Catalysis; D003500:Cyclization; D004224:Diterpenes / Q000737:chemistry; D007501:Iron / Q000737:chemistry*; D000081223:Polycyclic Sesquiterpenes; D013141:Spiro Compounds / Q000138:chemical synthesis*; D013237:Stereoisomerism; D013729:Terpenes / Q000737:chemistry
D000475:Alkenes; D004224:Diterpenes; D000081223:Polycyclic Sesquiterpenes; D013141:Spiro Compounds; D013729:Terpenes; C474511:elisabethin A; C078669:cedrol; D007501:Iron