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- aggregation classification "A1".
- aggregation creator person.
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- aggregation date "2011".
- aggregation format "application/pdf".
- aggregation hasFormat 1943641.bibtex.
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- aggregation isPartOf urn:issn:0022-3263.
- aggregation language "eng".
- aggregation rights "I have transferred the copyright for this publication to the publisher".
- aggregation subject "Chemistry".
- aggregation title "Stereoselective synthesis of cis-3,4-disubstituted piperidines through ring transformation of 2-(2-mesyloxyethyl)azetidines".
- aggregation abstract "The reactivity of 2-(2-mesyloxyethyl)azetidines, obtained through monochloroalane reduction and mesylation of the corresponding beta-lactams, with regard to different nucleophiles was evaluated for the first time, resulting in the stereoselective preparation of a variety of new 4-acetoxy-, 4-hydroxy-, 4-bromo-, and 4-formyloxypiperidines. During these reactions, transient 1-azoniabicyclo[2.2.0]hexanes were prone to undergo an S(N)2-type ring opening to afford the final azaheterocycles, which was rationalized by means of a detailed computational analysis. This approach constitutes a convenient alternative for the known preparation of 3,4-disubstituted 5,5-dimethylpiperidines, providing an easy access to the 5,5-nor-dimethyl analogues as valuable templates in medicinal chemistry. Furthermore, cis-4-bromo-3-(phenoxy or benzyloxy)piperidines were elaborated into the piperidin-3-one framework via dehydrobromination followed by acid hydrolysis.".
- aggregation authorList BK508619.
- aggregation endPage "8375".
- aggregation issue "20".
- aggregation startPage "8364".
- aggregation volume "76".
- aggregation aggregates 4133470.
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- aggregation similarTo jo201556t.
- aggregation similarTo LU-1943641.