Diastereoface-differentiating oxidation of 1-cyclohexenyl ether using a 2,4-pentanediol tether

Diastereoface-differentiating oxidation of the chiral enol ether prepared from cyclohexanone and optically active 2,4-pentanediol gave a diastereomeric mixture of the corresponding 2-hydroxycyclohexanone acetal. The diastereomeric excess of the product reached over 99% by oxidation with m-chloroperb...

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Bibliographic Details
Published in:Tetrahedron: asymmetry 1998-03, Vol.9 (6), p.1007-1013
Main Authors: Sugimura, Takashi, Iguchi, Hiromitsu, Tsuchida, Rumiko, Tai, Akira, Nishiyama, Norio, Hakushi, Tadao
Format: Article
Language:English
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Summary:Diastereoface-differentiating oxidation of the chiral enol ether prepared from cyclohexanone and optically active 2,4-pentanediol gave a diastereomeric mixture of the corresponding 2-hydroxycyclohexanone acetal. The diastereomeric excess of the product reached over 99% by oxidation with m-chloroperbenzoic acid at −78°C. Oxidation with t-butyl hydroperoxide in the presence of metal catalysts also resulted in high diastereomeric excesses of up to 97%.
ISSN:0957-4166
1362-511X
DOI:10.1016/S0957-4166(98)00046-9