Beilstein J. Org. Chem.2014,10, 3056–3072, doi:10.3762/bjoc.10.323
–Baylis–Hillman-type reaction [62]. Anodic methoxylation can be combined with biocatalytic approaches to prepare stereodivergent 4-hydroxypiperidines [63]. 3-Hydroxy-6-substituted piperidines inaccessible by conventional synthesis approaches can also be effectively synthesised by anodic methoxylation [64
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Graphical Abstract
Scheme 1:
Application of anodic oxidation to the generation of new carbon-carbon bonds [11].
Beilstein J. Org. Chem.2014,10, 369–383, doi:10.3762/bjoc.10.35
overcoming separation difficulties usually associated to triphenylphosphine oxide.
Keywords: amino acids; asymmetric synthesis; cyclodehydration; hydroxypiperidines; natural products; one-pot; Introduction
1,2-Amino alcohols of the type A (Figure 1) represent a frequent core motif of many pharmacologically
13b was obtained in only 63% yield (entry 3). The lower yield compared to the hydroxypiperidines 11a,b and 11d (≥74%, see Table 2) might be explained by the preference of a conformation of the phosphonium intermediate III of 11a,b and 11d (Scheme 5), which is favourable for the cyclisation. This
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Graphical Abstract
Figure 1:
Natural products and other bioactive piperidine derivatives of type B.