DIASTEREOFACE-DIFFERENTIATING OXIDATION OF 1-CYCLOHEXENYL ETHER USINGA 2,4-PENTANEDIOL TETHER

Authors
SUGIMURA T IGUCHI H TSUCHIDA R TAI A NISHIYAMA N HAKUSHI T
Citation
T. Sugimura et al., DIASTEREOFACE-DIFFERENTIATING OXIDATION OF 1-CYCLOHEXENYL ETHER USINGA 2,4-PENTANEDIOL TETHER, Tetrahedron : asymmetry, 9(6), 1998, pp. 1007-1013
Citations number
29
Categorie Soggetti
Chemistry Inorganic & Nuclear","Chemistry Inorganic & Nuclear","Chemistry Physical
Journal title
Tetrahedron : asymmetry → ACNP
ISSN journal
09574166
Volume
9
Issue
6
Year of publication
1998
Pages
1007 - 1013
Database
ISI
SICI code
0957-4166(1998)9:6<1007:DOO1EU>2.0.ZU;2-9
Abstract
Diastereoface-differentiating oxidation of the chiral enol ether prepa red from cyclohexanone and optically active 2,4-pentanediol gave a dia stereomeric mixture of the corresponding 2-hydroxycyclohexanone acetal . The diastereomeric excess of the product reached over 99% by oxidati on with m-chloroperbenzoic acid at -78 degrees C. Oxidation with t-but yl hydroperoxide in the presence of metal catalysts also resulted in h igh diastereomeric excesses of up to 97%. (C) 1998 Elsevier Science Lt d. All rights reserved.