ENANTIOSELECTIVE SYNTHESIS OF 2-ALLYL AND 3-TRIMETHYL-SILYLPROPARGYL)-2-HYDROXYCYCLOHEXANONE USING OSMIUM-CATALYZED ASYMMETRIC DIHYDROXYLATION

Authors
DEVAUX JM GORE J VATELE JM
Citation
Jm. Devaux et al., ENANTIOSELECTIVE SYNTHESIS OF 2-ALLYL AND 3-TRIMETHYL-SILYLPROPARGYL)-2-HYDROXYCYCLOHEXANONE USING OSMIUM-CATALYZED ASYMMETRIC DIHYDROXYLATION, Tetrahedron : asymmetry, 9(9), 1998, pp. 1619-1626
Citations number
22
Categorie Soggetti
Chemistry Inorganic & Nuclear","Chemistry Inorganic & Nuclear","Chemistry Physical
Journal title
Tetrahedron : asymmetry → ACNP
ISSN journal
09574166
Volume
9
Issue
9
Year of publication
1998
Pages
1619 - 1626
Database
ISI
SICI code
0957-4166(1998)9:9<1619:ESO2A3>2.0.ZU;2-L
Abstract
The catalytic asymmetric dihydroxylation of (1-cyclohexenyl) or (1-cyc lopentenyl) acetonitrile 5 and 15 with AD-mix-beta occurred with good enantiofacial selectivity (87 to 94.7% ee after recrystallization) giv ing (R,R)-diols in agreement with the mnemonic device. The 6-membered ring diol nitrile was easily transformed, via standard functional grou p manipulations, to 2-allyl and -trimethylsilylprop-2-ynyl)-2-hydroxyc yclohexanone in about 35% overall yield. (C) 1998 Elsevier Science Ltd . All rights reserved.