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|Title:||1-alkoxyamino-2-nitroalkanes as key building blocks for a chemo- and diastereoselective synthesis of a new type of polyfunctionalized N-alkoxypiperidine|
|Authors:||Lopez-Garcia, M. Angeles|
Fernandez-Bolanos, Jose G.
Organic compounds -- Synthesis
|Publisher:||Wiley - VCH Verlag|
|Citation:||Lopez-Garcia, M. A., Maya, I., Fernandez-Bolanos, J. G., Bosica, G., & Ballini, R. (2010). 1-alkoxyamino-2-nitroalkanes as key building blocks for a chemo- and diastereoselective synthesis of a new type of polyfunctionalized N-alkoxypiperidine. European Journal of Organic Chemistry, 2010, 28, 5482-5488.|
|Abstract:||A highly efficient conversion of β-nitrostyrenes into a new kind of functionalized N-alkoxy-2-hydroxypiperidine in two steps was developed, giving excellent yields and diastereoselectivity. The prepared compounds are the first examples of N-alkoxy-2-hydroxypiperidines. The synthetic approach involved the conjugate addition of alkoxyamines to β-nitrostyrenes, followed by Michael addition of the isolated nitroalkoxyamines to α,β-unsaturated carbonyl compounds, and intramolecular addition of the alkoxyamino group to the carbonyl functionality of the (non-isolated) adducts. Although three stereogenic centers are formed, only one diastereoisomer was detected. This unprecedented sequence of reactions can also be performed in a one-pot fashion.|
|Appears in Collections:||Scholarly Works - FacSciChe|
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