The synthesis of new five-membered enantiopure cyclic nitrones bearing protected cis vicinal amino and hydroxy functionalities is reported. The key step was a Mitsunobu reaction, which allowed placement of an azido group, with inversion of configuration, at the reacting centre. Cycloaddition of the novel nitrones to but-3-en-1-ol followed by simple elaboration of the adducts readily afforded protected amino dihydroxy indolizidines.
Synthesis of Enantiopure Protected 3-Hydroxy-4-Amino Pyrroline-N-Oxides / S. Cicchi; P. Ponzuoli; A. Goti; A. Brandi. - In: TETRAHEDRON LETTERS. - ISSN 0040-4039. - STAMPA. - 41:(2000), pp. 1583-1587. [10.1016/S0040-4039(99)02335-7]
Synthesis of Enantiopure Protected 3-Hydroxy-4-Amino Pyrroline-N-Oxides
CICCHI, STEFANO;GOTI, ANDREA;BRANDI, ALBERTO
2000
Abstract
The synthesis of new five-membered enantiopure cyclic nitrones bearing protected cis vicinal amino and hydroxy functionalities is reported. The key step was a Mitsunobu reaction, which allowed placement of an azido group, with inversion of configuration, at the reacting centre. Cycloaddition of the novel nitrones to but-3-en-1-ol followed by simple elaboration of the adducts readily afforded protected amino dihydroxy indolizidines.File | Dimensione | Formato | |
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