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2005
Pyridine derivatives
R 0380
Synthesis of Chiral Amino Epoxyaziridines: Useful Intermediates for the Preof Chiral Trisubstituted Piperidines. — Optically active oxiranylmethyl
04- 145 paration
aziridine (VIII) is prepared in good yield and with high diastereoselectivity starting
from serine-derived chloro ketone (I). Compound (VIII) undergoes in the presence of
LiClO4 successive openings of the oxirane and the aziridine rings by primary amines
(IX) at the less substituted carbons followed by ring closure to afford piperidines (X)
in totally chemoselective form. — (CONCELLON*, J. M.; RIEGO, E.; RIVERO, I.
A.; OCHOA, A.; J. Org. Chem. 69 (2004) 19, 6244-6248; Dep. Quim. Org. Inorg.,
Fac. Quim., Univ. Oviedo, E-33071 Oviedo, Spain; Eng.) — Klein
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