Title compounds represent interesting group of β-lactam antibiotics, β-lactamase and elastase inhibitors as well as activity against HCMV viruses.[1] Owing to their attractive biological activity, the synthesis of novel systems containing the b-lactam ring have been extensively investigated.[1]  

The most common strategy for the synthesis of such compounds involves nucleophilic substitution at C-4 of the 4-acetoxyazetidin-2-one ring.[2] We have shown previously that cinchona alkaloids are efficient catalyst in the synthesis of enantiomerically enriched 4-aryloxyazetidin-2-ones as well as 3,4-benzo-2-hydoxy-5-oxacephams.[3] We report herein enantioselective, quinidine mediated reaction affording the corresponding mono- and bicyclic b-lactams (Scheme 1).

The scope and limitations of such transformations will be briefly discussed.

[1] Veinberg, G.; Vorona, M.; Shestakova, I.; Kanepe, I.; Lukevics, E. Curr. Med. Chem. 2003, 10, 1741

[2] B. Furman, Z. Kałuża, A. Stencel, B. Grzeszczyk, M. Chmielewski,Topics in Heterocyclic Chemistry  7 (2007) 101.

[3] Kozioł, A. Frelek, J. Woźnica, M. Furman, B. Altieri, E. Chmielewski, M. J. Org. Chem, 2009, 74, 5687

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1. Diastereoselective Synthesis of β-Lactams via Kinugasa Reaction
2. From unsaturated sugar α,β-lactones to β-lactams. The synthesis. Od α,β-nienasyconych laktonów cukrowych do syntezy β-laktamów.
3. Cyclic Enaminones as Building Blocks in the Synthesis of Piperidine-Containing Natural Products and Biolo- gically Active Compounds
4. A Novel Method for the Synthesis of Ezetimibe Precursor
5.  Straightforward Methodology for the Stereoselective Synthesis of Benzo[a]- and Indolo[2,3-a]quinolizidines
6.  An entry to carbapenams via asymmetric Kinugasa reaction involving cyclic nitrones and terminal acetylenes
7. Reactions of diastereomeric sugar derived sulfites with sterically demanding organometallics
8. Polyhydroxylated indolizidine and pyrrolizidine alkaloids. Synthesis and bioactivity.
9. Strategies of the synthesis of oxa- and carba-penams and cephams