Premium
Synthetic applications of electrochemically produced α‐methoxyamides. Part 2 . Oxidation of hydroxyproline derivatives
Author(s) -
Thaning Mikkel,
Wistrand LarsG.
Publication year - 1986
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/hlca.19860690727
Subject(s) - chemistry , selectivity , electrochemistry , hydroxyproline , alcohol , kinetic control , derivative (finance) , organic chemistry , medicinal chemistry , electrode , catalysis , biochemistry , financial economics , economics
The electrochemical methoxylation of N ‐acetyl‐4‐hydroxyproline esters has been investigated. Both the free alcohol 3 and the corresponding 4‐acetoxy derivative 4 as well as the cis ‐4‐acetoxyproline 17 are methoxylated anodically preferentially at C(5), giving a mixture of stereoisomeric methoxy compounds. These mixtures can be used for further substitution as exemplified by the allylation of the methoxylated 4‐acetoxy derivatives, giving substitution products preferentially trans to the acetoxy group although with low selectivity. The low selectivity is discussed in terms of kinetic vs. thermodynamic control.