Organocatalytic enantioselective synthesis of nitrogen-substituted dihydropyran-2-ones, a key synthetic intermediate of 1β-methylcarbapenems

Organic Letters

Volumn 11, Issue 17, 2009, Pages 3934-3937

  Kobayashi, Shoji ^a,b,c   Kinoshita, Tatsuhiro ^a   Uehara, Hisatoshi ^b,c   Sudo, Tomoko ^b,c   Ryu, Llhyong ^a  

^a Osaka Prefecture University   (Japan)

^b MITSUBISHI CHEMICAL CORPORATION   (Japan)

^c API Corp   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 69449100082     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol901544q     Document Type: Article

References (37)

1. For a review on the synthesis of 1β-methylcarbapenem antibiotics, see: Berks, A. H. Tetrahedron 1996, 52, 331-375.
2. (a) Bayles, R.; Flynn, A. P.; Gait, R. H. B.; Kirby, S.; Turner, R. W. Tetrahedron Lett. 1988, 48, 6341-6344.
3. (b) Nishiuchi, M.; Honda, K.; Nakai, T. Chem. Lett. 1996, 321-322.
4. For a review on N-heterocyclic carbenes as organocatalysts, see: Enders, D.; Niemeier, O.; Henseler, A. Chem. Rev. 2007, 107, 5606-5655.
5. (a) He, M.; Uc, G. J.; Bode, J. W. J. Am. Chem. Soc. 2006, 128, 15088-15089.
6. (b) He, M.; Struble, J. R.; Bode, J. W. J. Am. Chem. Soc. 2006, 128, 8418-8420.
7. (c) He, M.; Beahm, B. J.; Bode, J. W. Org. Lett. 2008, 10, 3817-3820.
8. Crombie, L.; Games, D. E.; James, A. G. J. Chem. Soc., Perkin Trans. 1 1979, 464-471.
9. Leeming, P.; Ray, C. A.; Simpson, S. J.; Wallace, T. W.; Ward, R. A. Tetrahedron 2003, 59, 341-352.
10. Saito, S.; Uedo, E.; Kato, Y.; Murakami, Y.; Ishikawa, T. Synlett 1996, 1103-1105.
11. (a) Brochu, M. P.; Brown, S. P.; MacMillan, D. W. C. J. Am. Chem. Soc. 2004, 126, 4108-4109.
12. (b) Halland, N.; Braunton, A.; Bachmann, S.; Marigo, M.; Jørgensen, K. A. J. Am. Chem. Soc. 2004, 126, 4790-4791.
13. (c) Recently, a-chloroaldehyde bisulfite salts were identified as potential alternatives (see ref 4c).
14. Kerr, M. S.; Read de Alaniz, J.; Rovis, T. J. Org. Chem. 2005, 70, 5725-5728.
15. We initially performed the reaction with 0.5 mol % of the catalyst according to the original procedure. However, no 3,4-dihydropyran-2-ones were obtained, presumably due to the low reactivity of the amino-containing oxodienes.
16. 2a where (α-phenethylamide was incorporated as a carboxylic acid protecting group. In contrast, cycloaddition did not take place, and 4g was recovered unchanged. This is probably due to the inherent inertness of the trisubstituted Z-oxodiene arising from the bulkiness of the amide portion or strong hydrogen bonding between the amide proton and the carbonyl oxygen, causing an s-cis conformation which is disfavored for cycloaddition.
17. The influence of olefin geometry will become more apparent if the Z-isomers of 4a-f are submitted to cycloaddition. However, in our hands, those isomers could not be synthesized. We therefore do not exclude the case that isomerization occurs to generate the Z-isomer, which reacts rapidly with the catalytically generated enolate, leading to the observed stereochemistry.
18. For reviews on diarylprolinol ethers as organocatalysts, see: (a) List, B. Chem. Commun. 2006, 819-824.
19. (b) Marigo, M.; Jørgensen, K. A. Chem. Commun. 2006, 2001-2011.
20. (c) Guillena, G.; Ramón, D. J. Tetrahedron: Asymmetry 2006, 17, 1465-1492.
21. (d) Palomo, C.; Mielgo, A. Angew. Chem., Int. Ed. 2006, 45, 7876-7880.
22. For selected examples of enantioselective cycloadditions using diarylprolinol ether derivatives, see: (a) Juhl, K.; Jørgensen, K. A. Angew. Chem., Int. Ed. 2003, 42, 1498-1501.
23. (b) Samanta, S.; Krause, J.; Mandal, T.; Zhao, C.-G. Org. Lett. 2007, 9, 2745-2748.
24. (c) Wang, J.; Yu, F.; Zhang, X.; Ma, D. Org. Lett. 2008, 10, 2561-2564.
25. (d) Han, B.; Li, J.-L.; Ma, C.; Zhang, S.-J.; Chen, Y.-C. Angew. Chem., Int. Ed. 2008, 47, 9971-9974.
26. (e) Xie, H.; Zu, L.; Oueis, H. R.; Li, H.; Wang, J.; Wang, W. Org. Lett. 2008, 70, 1923-1926.
27. Amide-containing Z-oxodiene 4g was again unreactive in the enamine-catalyzed conditions.
28. Seebach, D.; Goliński, J. Helv. Chim. Acta 1981, 64, 1413-1423.
29. For selected examples of syra-selective Michael additions with diarylprolinol ether catalysts, see: (a) Hayashi, Y.; Gotoh, H.; Hayashi, T.; Shoji, M. Angew. Chem., Int. Ed. 2005, 44, A212-A215.
30. (b) Ender, D.; Hüttl, M. R. M.; Runsink, J.; Raabe, G.; Wendt, B. Angew. Chem., Int. Ed. 2007, 46, 467-469.
31. (c) Hayashi, Y.; Okano, T.; Aratake, S.; Hazelard, D. Angew. Chem., Int. Ed. 2007, 46, 4922-4925.
32. (d) Zhu, S.; Yu, S.; Ma, D. Angew. Chem., Int. Ed. 2008, 47, 545-548.
33. A concerted mechanism as proposed by Jørgensen et al. for the addition of aldehyde to enones cannot be ruled out.
34. (a) Bayles, R.; Flynn, A. P.; Gait, R. H. B.; Kirby, S.; Turner, R. W. Tetrahedron Lett. 1988, 29, 6345-6348.
35. (b) Hatanaka, M. Tetrahedron Lett. 1987, 28, 83-86.
36. (c) Udodong, U. E.; Fraser-Reid, B. J. Org. Chem. 1988, 53, 2131-2132.
37. Detailed NMR analysis indicated that two of the products were not lactones, but acyclic reduction products, namely precursors of lactone.