Dihydroxylation of Polyenes Using Narasaka's Modification of the Upjohn Procedure.
Dihydroxylation of a variety of commercially available polyenes has been investigated using phenylboronic acid, N-methylmorpholine N-oxide (NMO), and osmium tetroxide in anhydrous solvent. The diastereoselectivity of multiple oxidation steps is in some cases affected by the in situ protection of the intermediate ene-diols as phenyboronic esters, affording polyols not available from the standard Upjohn dihydroxylation procedure. A convenient oxidative deprotection of the phenylboronic esters is also described.
Gypser
Andreas
A
Department of Chemistry and Skaggs Institute for Chemical Biology, The Scripps Research Institute, 10550 N Torrey Pines Rd, La Jolla, California 92037.
Michel
Dominique
D
Nirschl
David S.
DS
Sharpless
K. Barry
KB