Enantio- and Diastereoselective Synthesis of Piperidines by Coupling of Four Components in a “One-Pot” Sequence Involving Diphenylprolinol Silyl Ether Mediated Michael Reaction

An efficient, asymmetric, four-component, one-pot synthesis of highly substituted piperidines with excellent diastereo- and enantioselectivity was established through the diphenylprolinol silyl ether mediated Michael reaction of aldehyde and nitroalkene, followed by the domino aza-Henry reaction/hem...

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Bibliographic Details
Published in:Organic letters 2010-10, Vol.12 (20), p.4588-4591
Main Authors: Urushima, Tatsuya, Sakamoto, Daisuke, Ishikawa, Hayato, Hayashi, Yujiro
Format: Article
Language:English
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Summary:An efficient, asymmetric, four-component, one-pot synthesis of highly substituted piperidines with excellent diastereo- and enantioselectivity was established through the diphenylprolinol silyl ether mediated Michael reaction of aldehyde and nitroalkene, followed by the domino aza-Henry reaction/hemiaminalization reaction and a Lewis acid mediated allylation or cyanation reaction. All carbons of the piperidine ring are substituted with different groups, and its five contiguous stereocenters are completely controlled in both relative and absolute senses.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol1018932