title: Dihydroxylation of Polyenes Using Narasaka's Modification of the Upjohn Procedure.
abstract: 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.
authors.affiliation: Department of Chemistry and Skaggs Institute for Chemical Biology, The Scripps Research Institute, 10550 N Torrey Pines Rd, La Jolla, California 92037.
authors.forename: Andreas
authors.initials: A
authors.lastname: Gypser
authors.forename: Dominique
authors.initials: D
authors.lastname: Michel
authors.forename: David S.
authors.initials: DS
authors.lastname: Nirschl
authors.forename: K. Barry
authors.initials: KB
authors.lastname: Sharpless