Electrooxidative coupling of furans and silyl enol ethers: application to the synthesis of annulated furans.
The preparation of annulated furan systems as key synthetic intermediates through the application of a two-step annulation involving an electrochemical ring closure between a furan and a silyl enol ether has been studied. The reaction was shown to be quite general for the formation of six-membered rings in good yields and was tolerant of a variety of different functional groups. The ring closure was highly stereoselective, leading to the formation of cis-fused systems. Cyclic voltammetry and probe molecules were used to gain mechanistic insight into the reaction. These studies suggested that the key ring closure involved an initial oxidation of the silyl enol ether to a radical cation followed by a furan-terminated cyclization.
Sperry
Jeffrey B
JB
Department of Chemistry, Dartmouth College, Hanover, New Hampshire 03755, USA.
Whitehead
Christopher R
CR
Ghiviriga
Ion
I
Walczak
Ryan M
RM
Wright
Dennis L
DL