DIHYDROXYLATION OF POLYENES USING NARASAKAS MODIFICATION OF THE UPJOHN PROCEDURE

Authors
GYPSER A MICHEL D NIRSCHL DS SHARPLESS KB
Citation
A. Gypser et al., DIHYDROXYLATION OF POLYENES USING NARASAKAS MODIFICATION OF THE UPJOHN PROCEDURE, Journal of organic chemistry, 63(21), 1998, pp. 7322-7327
Citations number
19
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Journal of organic chemistry → ACNP
ISSN journal
00223263
Volume
63
Issue
21
Year of publication
1998
Pages
7322 - 7327
Database
ISI
SICI code
0022-3263(1998)63:21<7322:DOPUNM>2.0.ZU;2-M
Abstract
Dihydroxylation of a variety of commercially available polyenes has be en investigated using phenylboronic acid, N-methylmorpholine N-oxide ( NMO), and osmium tetroxide in anhydrous solvent. The diastereoselectiv ity of multiple oxidation steps is in some cases affected by the in si tu protection of the intermediate ene-diols as phenyboronic esters, af fording polyols not available from the standard Upjohn dihydroxylation procedure. A convenient oxidative deprotection of the phenylboronic e sters is also described.