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2005
Azetidine derivatives
R 0045
Rearrangement of 4-(1-Haloalkyl)- and 4-(2-Haloalkyl)-2-azetidinones into Methyl ω-Alkylaminopentenoates via Transient Aziridines and Azetidines. — Treat01- 090 ment
of haloimines of type (I) and (IX) with ketenes results in stereoselective formation
of new cis-substituted β-lactams such as (III) and (X). In the presence of an excess of
NaOMe, the β-lactams without a quaternary center at C4 undergo rearrangement to 4or 5-aminopentenoates. This rearrangement proceeds via aziridine or azetidine intermediates which can be isolated under acidic conditions. — (DEJAEGHER, Y.; DE
KIMPE*, N.; J. Org. Chem. 69 (2004) 18, 5974-5985; Dep. Org. Chem., Fac. Agric.
Appl. Biol. Sci., Univ. Gent, B-9000 Gent, Belg.; Eng.) — Jannicke
2005
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