ASYMMETRIC-SYNTHESIS OF CYCLOHEX-2-ENOLS - THE EXAMPLES OF SEUDENOL AND ANALOGS

Authors
BUENO AB CARRENO MC RUANO JLG HAMDOUCHI C
Citation
Ab. Bueno et al., ASYMMETRIC-SYNTHESIS OF CYCLOHEX-2-ENOLS - THE EXAMPLES OF SEUDENOL AND ANALOGS, Tetrahedron : asymmetry, 6(6), 1995, pp. 1237-1240
Citations number
28
Categorie Soggetti
Chemistry Inorganic & Nuclear","Chemistry Inorganic & Nuclear","Chemistry Physical
Journal title
Tetrahedron : asymmetry → ACNP
ISSN journal
09574166
Volume
6
Issue
6
Year of publication
1995
Pages
1237 - 1240
Database
ISI
SICI code
0957-4166(1995)6:6<1237:AOC-TE>2.0.ZU;2-X
Abstract
An efficient Synthesis of enantiomerically pure cyclohex-2-enols from the reaction of 2-p-tolylsulfinyl cyclohexanols with (CF3CO)(2)O/Py an d subsequent hydrogenolysis of the C-S bond with Li/Naphthalene, is re ported. This strategy has been applied to the asymmetric synthesis of seudenol and 1-methylcyclohex-2-en-1-ol. New data on the rearrangement of the trifluoroacetate group when 2-p-tolylsulfinyl-1-methylcyclohex enols are treated under the Pummerer reaction conditions are also repo rted.