Synthesis of piperidin-4-ones starting from 2-(2-bromo-1,1-dimethylethyl)azetidines and 2-(2-mesyloxyethyl)azetidines through a ring expansion–oxidation protocol
作者： Karen Mollet , Matthias D'hooghe , Leen Broeckx , Barbara Danneels , Tom Desmet
DOI: 10.1016/J.TET.2013.01.045
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摘要: Abstract cis-2-(2-Bromo-1,1-dimethylethyl)azetidines were transformed into novel 5,5-dimethylpiperidin-4-ones through a ring expansion–oxidation protocol upon heating in DMSO the presence of Ag2CO3 or AgBF4. In addition, several 5,5-nor-dimethyl analogues latter piperidin-4-ones synthesized selective way similar approach involving treatment cis-2-(2-mesyloxyethyl)azetidines with K2CO3 DMSO. Furthermore, both diastereoselective and an enantioselective reduction carbonyl function performed chemical enzymatic approach, respectively. Whereas NaBH4-induced reduction proceeded cis-diastereoselectivity, alcohol dehydrogenase-mediated reductions resulted either S- R-enantioselectivity.
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