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Dihydroxylation of Polyenes Using Narasaka's Modification of the Upjohn Procedure
Andreas Gypser1, Dominique Michel, David S. Nirschl
1Department of Chemistry and Skaggs Institute for Chemical Biology, The Scripps Research Institute, 10550 N Torrey Pines Rd, La Jolla, California 92037.
The Journal of Organic Chemistry
|October 24, 2001
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.