Tetrahedron Letters p. 3103 - 3104 (1994)
Update date:2022-07-30
Topics:
Kato, Keisuke
Suemune, Hiroshi
Sakai, Kiyoshi
Oxidation of chiral β'-trimethylsilyloxy enol ethers 2a-d and β'-hydroxy enol ethers 3a-e, prepared from the corresponding β-keto esters, with MCPBA afforded α-hydroxy esters (4a-d and 5a-e) in a highly diasteroselective manner.The absolute configurations of the newly generated stereogenic center in 4 and 5 were found to be contrary.Key Words: (S,S)-cyclohexane-1,2-diol; (S,S)-cycloheptane-1,2-diol; asymmetric oxidation, asymmetric epoxydation; chiral auxiliary, chiral enol ether
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