The copper(I) mediated reaction of nitrones and terminal acetylenes, which is known as Kinugasa reaction, represents an attractive method of direct formation of the β-lactam ring.[1,2] This reaction can be performed in many ways including diastereo- and enantioselective versions. In most cases, as 1,3-dipoles simple acyclic nitrones have been used.[3] Number of reactions involving cyclic ones is limited.

Herein, we present our recent studies on Kinugasa reaction involving cyclic nitrones readily available from hydroxy acids or amino acids and terminal acetylenes either achiral or bearing a stereogenic center.[4] All investigated reactions proceeded in good yield and with high diastereoselectivity providing an attractive entry to carbapenams of a potential biological activity.[5] The stereochemical pathway of the reaction and influence of geometry and substitutions in one or both reactants on direction and magnitude of asymmetric induction will be discussed.

REFERENCES

[1] (a) M. Kinugasa, S. Hashimoto, J. Chem. Soc., Chem. Commun. 1972, 466–467, (b) R. Pal, S. Ghosh, K. Chandra, A. Basak, Synlett 2007, 2321–2330.

[2] A. Brandi, S. Cicchi, F. Cordero, Chem. Rev. 2008, 108, 3988-4035.

[3] (a) M. Miura, M. Enna, K. Okuro, M. Nomura, J. Org. Chem. 1995, 18, 4999–5004; (b) M. Lo, G. Fu, J. Am. Chem. Soc. 2002, 124, 4572–4573; (c) M.-C. Ye, J. Zhou, Y. Tang, J. Org. Chem. 2006, 71, 3576–3582.

[4] (a) S. Stecko, A. Mames, B. Furman, M. Chmielewski, J. Org. Chem. 2008, 73, 7402-7404; (b) S. Stecko, A. Mames, B. Furman, M. Chmielewski, J. Org. Chem. 2009, 74, 3094-3100.

[5] Chemistry and Biology of β-Lactam Antibiotics, M. Morin, M. Gorman, Eds., Wiley-VCH, New York, 1982

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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. An asymmetric synthesis of 4-aryloxyazetidin-2-ones and 3,4-benzo-2-hydroxycephams
4. Cyclic Enaminones as Building Blocks in the Synthesis of Piperidine-Containing Natural Products and Biolo- gically Active Compounds
5. A Novel Method for the Synthesis of Ezetimibe Precursor
6.  Straightforward Methodology for the Stereoselective Synthesis of Benzo[a]- and Indolo[2,3-a]quinolizidines
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