Tetrahedron p. 1411 - 1424 (1996)
Update date:2022-08-02
Topics:
Jurczak, Margarita
Socha, Dariusz
Chmielewski, Marek
Conjugate addition - rearrangement of N-benzylhydroxylamine to α,β-unsaturated lactones 1 provides a short and effective route to 3-substituted isoxazolidin-5-ones. High and defined stereochemistry of this reaction with simulataneous liberation of the 5-OH group of the sugar chain, while all other groups remain protected, creates a possibility to switch from sugars of the D-configurational series to those of the L-series, thus providing a very attractive entry to important 3-amino-2,3-dideoxy sugars. Mesylation of the 2'-OH group of the isoxazolidin-5-one skeleton or introduction of an epoxide ring to C-2',3' carbon atoms and subsequent treatment of the molecule with a nucleophile causes isoxazolidin-5-one - isoxazolidine rearrangement with inversion of the configuration at the C-2 carbon atom.
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Doi:10.1016/0960-894X(96)00001-7
(1996)Doi:10.1016/0022-328X(95)05865-M
(1996)Doi:10.1016/0040-4039(95)02278-3
(1996)Doi:10.1016/S0040-4039(00)71644-3
(1967)Doi:10.1021/jm950918e
(1996)Doi:10.1016/0040-4039(96)00117-7
(1996)