Dihydroxylation of Polyenes Using Narasaka's Modification of the Upjohn Procedure

…, D Michel, DS Nirschl, KB Sharpless

Index: Gypser, Andreas; Michel, Dominique; Nirschl, David S.; Barry Sharpless Journal of Organic Chemistry, 1998 , vol. 63, # 21 p. 7322 - 7327

Full Text: HTML

Citation Number: 30

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 ...