Asymmetric Synthesis of trans-3-Amino-4-alkylazetidin-2-ones from Chiral N,N-Dialkylhydrazones

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 cleavag...

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Bibliographic Details
Published in:Organic letters 2004-08, Vol.6 (16), p.2749-2752
Main Authors: Díez, Elena, Fernández, Rosario, Marqués-López, Eugenia, Martín-Zamora, Eloísa, Lassaletta, José M
Format: Article
Language:English
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Summary: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.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol0490328