An efficient synthesis of de novo imidates via aza-Claisen rearrangements of N-allyl ynamides

Synlett

Volumn , Issue 16, 2010, Pages 2397-2402

  Dekorver, Kyle A ^a   North, Troy D ^a   Hsung, Richard P ^a  

^a UNIVERSITY OF WISCONSIN MADISON   (United States)

Author keywords

aza Claisen; imidate; ketenimine; Overman rearrangement; ynamide

Indexed keywords

ALPHA ALLYLIMIDATE DERIVATIVE; AMIDINE; NUCLEOPHILE; PALLADIUM; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CLAISEN REARRANGEMENT; DRUG SYNTHESIS;

EID: 77957164556     PISSN: 09365214     EISSN: 14372096     Source Type: Journal    
DOI: 10.1055/s-0030-1258544     Document Type: Article

References (39)

1. For reviews, see:, DeKorver K A., Li H, Lohse A G., Hayashi R, Lu Z, Zhang Y, Hsung R P., Chem. Rev. 2010 110 in press
2. Evano G, Coste A, Jouvin K, Angew. Chem. Int. Ed. 2010 49 2840
3. For examples in 2010, see:, Li H, Antoline J E., Yang J.-H, Al-Rashid Z F., Hsung R P., New J. Chem. 2010 34 in press
4. Kramer S, Madsen J L. H., Rottlnder M, Skrydstrup T, Org. Lett. 2010 12 2758
5. Banerjee B, Litvinov D N., Kang J, Bettale J D., Castle S L., Org. Lett. 2010 12 2650
6. Gourdet B, Rudkin M E., Lam H W., Org. Lett. 2010 12 2554
7. Jia W, Jiao N, Org. Lett. 2010 12 2000
8. Burley G A., Davies D L., Griffith G A., Lee M, Singh K, J. Org. Chem. 2010 75 980
9. Yamasaki R, Terashima N, Sotome I, Komagawa S, Saito S, J. Org. Chem. 2010 75 480
10. Zhang Y, DeKorver K A., Lohse A G., Zhang Y.-S, Huang J, Hsung R P., Org. Lett. 2009 11 899
11. DeKorver K A., Hsung R P., Lohse A G., Zhang Y, Org. Lett. 2010 12 1840
12. For leading reviews on aza-Claisen rearrangements, see
13. Majumdar K C., Bhayyacharyya T, Chattopadhyay B, Nandi R K., Synthesis 2009 2117
14. Nubbemeyer U, Top Curr. Chem. 2005 244 149
15. Majumdar K C., Samanta S, Chattopadhyay B, Nandi R K., Synthesis 2010 863
16. Cheung L L. W., Yudin A K., Org. Lett. 2009 11 1281
17. Cant A A., Bertrand G H. V., Henderson J L., Roberts L, Greaney M F., Angew. Chem. Int. Ed. 2009 48 5199
18. For reviews on the chemistry of ketenimines, see:, Krow G R., Angew. Chem., Int. Ed. Engl. 1971 10 435
19. Gambaryan N P., Usp. Khim. 1976 45 1251
20. Dondoni A, Heterocycles 1980 14 1547
21. Barker M W., McHenry W E., In The Chemistry of Ketenes, Allenes and Related Compounds Part 2 Patai S Wiley-Interscience Chichester 1980 701-720
22. Alajarin M, Vidal A, Tovar F, Targets Heterocycl. Syst. 2000 4 293
23. For examples of imidates serving as prodrugs, see:, Maryanoff B E., McComsey D F., Costanzo M J., Yabut S C., Lu T, Player M R., Giardino E C., Damiano B P., Chem. Biol. Drug. Des. 2006 68 29
24. Poon S F., Stock N, Payne J E., McGuire A R., Stearns B, Yang X, Chen W, Munoz B, Smith N D., Bioorg. Med. Chem. Lett. 2005 15 2259
25. Bundgaard H, DrustrupLarsen J, J. Med. Chem. 1988 31 2066
26. For recent examples of amidine formation, see:, Shang Y, He X, Hu J, Wu J, Zhang M, Yu S, Zhang Q, Adv. Synth. Catal. 2009 351 2709
27. She J, Jiang Z, Wang Y, Synlett 2009 2023
28. Yu R T., Rovis T, J. Am. Chem. Soc. 2008 130 3262
29. Yoo E J., Ahlquist M, Bae I, Sharpless B, Fokin V, Chang S, J. Org. Chem. 2008 73 5520
30. For recent examples of imidate formation, see:, Song W, Lu W, Wang J, Lu P, Wang Y, J. Org. Chem. 2010 75 3481
31. Yoo E J., Park S H., Lee S H., Chang S, Org. Lett. 2009 11 1155
32. Yoo E J., Bae I, Cho S H., Han H, Chang S, Org. Lett. 2006 8 1347
33. For a recent example of -functionalization of imidates, see:, Matsubara R, Berthiol F, Kobayashi S, J. Am. Chem. Soc. 2008 130 1804
34. For a related 1,3-shift, see:, Bendikov M, Duong H M., Bolanos E, Wudl F, Org. Lett. 2005 7 783
35. For leading references, see:, Anderson C E., Overman L E., J. Am. Chem. Soc. 2003 125 12412
36. For a review, see:, Overman L E., Acc. Chem. Res. 1980 13 218
37. Overman L E., J. Am. Chem. Soc. 1974 96 597
38. Overman L E., J. Am. Chem. Soc. 1976 98 2901
39. Tomooka K, Suzuki M, Uehara K, Shimada M, Akiyama T, Synlett 2008 2518