Diastereoselective synthesis of bicyclic gamma-lactams via ring expansion of monocyclic beta-lactams

The Journal of Organic Chemistry
Stijn DekeukeleireNorbert De Kimpe

Abstract

cis-4-(1-Chloro-1-methylethyl)-1-(omega-hydroxyalkyl)azetidin-2-ones were diastereoselectively transformed into novel trans-1-aza-4-oxabicyclo[3.3.0]octan-8-ones and trans-1-aza-5-oxabicyclo[4.3.0]nonan-9-ones upon treatment with 1 equiv of AgBF4 and pyridine in toluene via intramolecular nucleophilic trapping of N-acyliminium intermediates by the hydroxyl moiety. Additionally, the corresponding aza-analogues of the aforementioned bicyclic gamma-lactams (i.e., trans-1,4-diazabicyclo[3.3.0]octan-8-ones and trans-1,5-diazabicyclo[4.3.0]nonan-9-ones) were prepared in a convenient way starting from cis-4-(1-chloro-1-methylethyl)-1-{omega-[(tert-butoxycarbonyl)amino]alkyl}azetidin-2-ones applying the same reaction conditions. The intermediate N-acyliminium ions were formed by ring expansion of the starting beta-lactams through generation of a transient silver(I)-induced carbenium ion.

References

Jan 1, 1991·The Journal of Antibiotics·J E BaldwinJ Pitlik
Jul 10, 2001·The Journal of Organic Chemistry·R C Desai
Apr 2, 2002·The Journal of Organic Chemistry·Yves DejaegherNorbert De Kimpe
Apr 23, 2005·The Journal of Organic Chemistry·Willem Van Brabandt, Norbert De Kimpe
Mar 14, 2007·Current Topics in Medicinal Chemistry·Jens-Uwe Peters
May 17, 2007·Journal of the American Chemical Society·William L ScottMartin J O'Donnell

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Citations

May 12, 2017·Chemical Reviews·Peng Wu, Thomas E Nielsen
Apr 18, 2012·Beilstein Journal of Organic Chemistry·Rob De Vreese, Matthias D'hooghe
Sep 24, 2020·Chemical Communications : Chem Comm·Sangh Priya SinghAjay Kumar Srivastava
Jan 30, 2014·Organic & Biomolecular Chemistry·Long-Wu YeFabien Gagosz
Jun 20, 2019·Chemical Communications : Chem Comm·Dong ChenChen Zhu
Jun 24, 2017·ChemistryOpen·Sari DeketelaereMatthias D'hooghe
Jun 30, 2011·Organic Letters·Sébastien ComesseAdam Daïch
Apr 20, 2012·Organic Letters·Richard S GraingerSimon J Coles

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