(R)-2,3-Cyclohexylideneglyceraldehyde: a novel template for simple entry into both cis- and trans-2,5-disubstituted tetrahydrofurans

Sharpless asymmetric dihydroxylation at the terminal olefin of benzoates 3a and 3b, using both AD-mix α and AD-mix β afforded only one diastereomer of diols 5a and 5b, respectively. Diols 5a and 5b were easily transformed into cis- and trans-2,5-disubstituted tetrahydrofurans 7 and 14, respectively, which were subsequently converted into known compounds 12 and 19.