Highly efficient Rh(I) and Ir(I) single and dual metal catalysed dihydroalkoxylation reactions of alkyne diols.
A highly efficient rhodium(I) and iridium(I) catalysed dihydroalkoxylation reaction of alkyne diols is employed here for the synthesis of spiroketals and a fused bicyclic ketal. The two metal catalysts show differential selectivity and efficiency for either the cyclisation of the 5-exo or 6-endo-membered rings. For the first time, a dual metal (Rh and Ir) catalyst system is effectively utilised for the formation of the 5,6-spiroketals, more efficiently than the single metal catalysts. The two different metals create a dual activation pathway to enhance the 5- and 6-membered ring closure as compared with the equivalent single catalysts.
Ho
Joanne Hui Hui
JH
School of Chemistry, University of New South Wales, Kensington, NSW 2052, Australia.
Hodgson
Richard
R
Wagler
Jörg
J
Messerle
Barbara Ann
BA
D000480:Alkynes / Q000737:chemistry*; D002384:Catalysis; D056831:Coordination Complexes / Q000138:chemical synthesis / Q000737:chemistry; D018360:Crystallography, X-Ray; D003500:Cyclization; D005663:Furans / Q000138:chemical synthesis / Q000737:chemistry*; D007495:Iridium / Q000737:chemistry*; D008968:Molecular Conformation; D012238:Rhodium / Q000737:chemistry*; D013141:Spiro Compounds / Q000138:chemical synthesis / Q000737:chemistry*; D013237:Stereoisomerism
D000480:Alkynes; D056831:Coordination Complexes; D005663:Furans; D013141:Spiro Compounds; C520774:spiroketal; D007495:Iridium; D012238:Rhodium