Diastereoselective protocols for the synthesis of 2,3 trans- and 2,3 ci6-methoxy-morpholine-2-carboxylic acid derivatives
Articolo
Data di Pubblicazione:
2012
Citazione:
Diastereoselective protocols for the synthesis of 2,3 trans- and 2,3 ci6-methoxy-morpholine-2-carboxylic acid derivatives / M. Penso, F. Foschi, S. Pellegrino, A. Testa, M.L. Gelmi. - In: JOURNAL OF ORGANIC CHEMISTRY. - ISSN 0022-3263. - 77:7(2012), pp. 3454-3461.
Abstract:
Two diastereoselective and straightforward protocols for the high-yielding synthesis of 2,3-trans- and 2,3-cis-6-methoxy-3-substituted morpholine-2- carboxylic esters were realized in few steps, through the condensation between 5,6-diethoxy-5,6-dimethyl-1,4-dioxan-2-one and an appropriate imine, which is the key reaction to control the C2-C3 relative stereochemistry, followed by a methanolysis/ring-closure tandem reaction sequence. In particular, 2,3-trans-morpholines derive from the R*,S*-product of the acid condensation of N-functionalized alkylimines with the silylketene acetal of the above lactone, whereas 2,3-cis-morpholines derive from the R*,R*- product of basic condensation of an N-tosylimines with the lactone.
Tipologia IRIS:
01 - Articolo su periodico
Elenco autori:
M. Penso, F. Foschi, S. Pellegrino, A. Testa, M.L. Gelmi
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