Helvetica Chimica Acta p. 1711 - 1717 (1986)
Update date:2022-08-03
Topics:
Thaning, Mikkel
Wistrand, Lars-G.
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.
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Doi:10.1021/om8008475
(2009)Doi:10.1002/ejoc.200800684
(2008)Doi:10.1055/s-1986-31753
(1986)Doi:10.1016/S0040-4039(00)82412-0
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(2009)Doi:10.1002/anie.201812836
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