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Synlett 2001; 2001(10): 1531-1534
DOI: 10.1055/s-2001-17453
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Dual Behavior of 2-Azetidinone-Tethered Arylimines as Azadienophiles or Azadienes. Application to the Asymmetric Synthesis of Indolizidine-Type Systems

Benito Alcaide* , Pedro Almendros, Jose M. Alonso, Moustafa F. Aly, M. Rosario Torres
  • *Departamento de Química Orgánica I, Facultad de Química, Universidad Complutense, 28040-Madrid, Spain; Fax + 34(91)3 94 41 03; E-mail: alcaideb@eucmax.sim.ucm.es
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Publication Date:
27 September 2001 (online)

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The first methodology to prepare indolizidine systems directly from β-lactams has been developed. This process involves the amide bond cleavage of the β-lactam ring in the aza Diels-Alder cycloadducts with concomitant cyclization. Indolizidinone precursors arise from normal, as well as inverse electron-demand condensation involving the C=N moiety of 2-azetidinone-tethered imines as the dienophile or the heterodiene contributor.

lactams - aza Diels-Alder cycloaddition - rearrangement - indolizidines - asymmetric synthesis

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