Asymmetric synthesis of trans-3-amino-4-alkylazetidin-2-ones from chiral N,N-dialkylhydrazones

Elena Díez; Rosario Fernández; Eugenia Marqués-López; Eloísa Martín-Zamora; José M Lassaletta

doi:10.1021/ol0490328

Asymmetric synthesis of trans-3-amino-4-alkylazetidin-2-ones from chiral N,N-dialkylhydrazones

Org Lett. 2004 Aug 5;6(16):2749-52. doi: 10.1021/ol0490328.

Authors

Elena Díez¹, Rosario Fernández, Eugenia Marqués-López, Eloísa Martín-Zamora, José M Lassaletta

Affiliation

¹ Instituto de Investigaciones Químicas, CSIC-USe, c/Américo Vespucio s/n, Isla de la Cartuja, E-41092 Seville, Spain.

PMID: 15281760
DOI: 10.1021/ol0490328

Abstract

Enantiopure N,N-dialkylhydrazones 3 smoothly react with N-benzyloxycarbonyl-N-benzyl glycine as an aminoketene precursor to afford trans-3-amino-4-alkylazetidin-2-ones 4 as single diasteromers. As an exception, hydrazone 3f (R = OBn) affords cis-(3R,4R)-4f under modified conditions. N-N Bond cleavage of cycloadducts 4 afforded free azetidinones 5 in high yields. [structure: see text]