Au-catalyzed cyclization of monopropargylic triols: an expedient synthesis of monounsaturated spiroketals.
The gold-catalyzed cyclization of monopropargylic triols to form olefin-containing spiroketals is reported. The reactions are rapid and high yielding when 2 mol % of the catalyst generated in situ from Au[P(t-Bu)(2)(o-biphenyl)]Cl and AgOTf is employed in THF at 0 degrees C. A range of differentially substituted triols leading to substituted 5- and 6-membered ring spiroketals were prepared and function well in the reaction.
Aponick
Aaron
A
Department of Chemistry, University of Florida, Gainesville, Florida 32611, USA. aponick@chem.ufl.edu
Li
Chuan-Ying
CY
Palmes
Jean A
JA
D000480:Alkynes / Q000737:chemistry*; D002384:Catalysis; D005663:Furans / Q000138:chemical synthesis* / Q000737:chemistry; D006046:Gold / Q000737:chemistry*; D015394:Molecular Structure; D050607:Organogold Compounds / Q000737:chemistry*; D020005:Propanols / Q000737:chemistry*; D013141:Spiro Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
D000480:Alkynes; D005663:Furans; D050607:Organogold Compounds; D020005:Propanols; D013141:Spiro Compounds; C520774:spiroketal; D006046:Gold