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Synfacts 2008(5): 0467-0467
DOI: 10.1055/s-2008-1072695
DOI: 10.1055/s-2008-1072695
Synthesis of Heterocycles
© Georg Thieme Verlag Stuttgart · New York
Synthesis of 4-Hydroxypipecolic Acid β-Lactam Analogues from Oxoazetidines
B. Alcaide*, P. Almendros*, A. Luna, T. Martínez del Campo
Universidad Complutense de Madrid and CSIC, Madrid, Spain
Weitere Informationen
Publikationsverlauf
Publikationsdatum:
23. April 2008 (online)

Significance
Two different stereocontrolled aminocyclization routes from 3-azidoallenol-4-oxoazetidine-2-carbaldehyde 2 to new 4-hydroxypipecolic acid β-lactam analogues 6 and 8 are described. The route from 2 to 6 involves a key indium-mediated Barbier-type carbonyl-allenylation reaction, followed by alcohol protection, reduction of azide to amine and finally aminocyclization. The route from 2 to 8 entails an organocatalytic (l-proline) aldol reaction followed by hydrogenation and aminocyclization. Enantiopure compound 1 is reported.