Stereoselective synthesis of indolines via organocatalytic thioester enolate addition reactions

Organic Letters

Volumn 16, Issue 16, 2014, Pages 4236-4239

  Kolarovic, Andrej ^a   Käslin, Alexander ^a   Wennemers, Helma ^a  

^a ETH ZURICH   (Switzerland)

Author keywords

[No Author keywords available]

Indexed keywords

ACETIC ACID DERIVATIVE; CARBOXYLIC ACID; INDOLE DERIVATIVE; INDOLINE;

CATALYSIS; CHEMICAL STRUCTURE; CHEMISTRY; STEREOISOMERISM; SYNTHESIS;

ACETATES; CARBOXYLIC ACIDS; CATALYSIS; INDOLES; MOLECULAR STRUCTURE; STEREOISOMERISM;

EID: 84906250132     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol501936n     Document Type: Article

References (40)

1. Modern Alkaloids; Fattorusso, E., Taglialatela-Scafati, O., Eds.; Wiley-VCH: Weinheim, 2008.
2. Natural Products; Ramawat, K. G., Mérillon, J.-M., Eds.; Springer-Verlag: Heidelberg, 2013.
3. Pietruszka, J.; Simon, R. C. ChemCatChem 2010, 2, 505-508
4. Asami, M.; Watanabe, H.; Honda, K.; Inoue, S. Tetrahedron: Asymmetry 1998, 9, 4165-4173
5. Kuwano, R.; Sato, K.; Kurokawa, T.; Karube, D.; Ito, Y. J. Am. Chem. Soc. 2000, 122, 7614-7615
6. Kuwano, R.; Kaneda, K.; Ito, T.; Sato, K.; Kurokawa, T.; Ito, Y. Org. Lett. 2004, 6, 2213-2215
7. Kuwano, R.; Kashiwabara, M.; Sato, K.; Ito, T.; Kaneda, K.; Ito, Y. Tetrahedron: Asymmetry 2006, 17, 521-535
8. Kuwano, R.; Kashiwabara, M. Org. Lett. 2006, 8, 2653-2655
9. Li, C.; Chen, J.; Fu, G.; Liu, D.; Liu, Y.; Zhang, W. Tetrahedron 2013, 69, 6839-6844
10. Xiao, Y.-C.; Wang, C.; Yao, Y.; Sun, J.; Chen, Y.-C. Angew. Chem., Int. Ed. 2011, 50, 10661-10664
11. Teller, H.; Corbet, M.; Mantilli, L.; Gopakumar, G.; Goddard, R.; Thiel, W.; Fürstner, A. J. Am. Chem. Soc. 2012, 134, 15331-15342
12. Hashimoto, T.; Yamamoto, K.; Maruoka, K. Chem. Commun. 2014, 50, 3220-3223
13. Bailey, W. F.; Mealy, M. J. J. Am. Chem. Soc. 2000, 122, 6787-6788
14. Gil, G. S.; Groth, U. M. J. Am. Chem. Soc. 2000, 122, 6789-6790
15. Bailey, W. F.; Luderer, M. R.; Mealy, M. J. Tetrahedron Lett. 2003, 44, 5303-5305
16. Mealy, M. J.; Luderer, M. R.; Bailey, W. F.; Sommer, M. B. J. Org. Chem. 2004, 69, 6042-6049
17. Curran, D. P.; Chen, C. H.-T.; Geib, S. J.; Lapierre, A. J. B. Tetrahedron 2004, 60, 4413-4424
18. Petit, M.; Geib, S. J.; Curran, D. P. Tetrahedron 2004, 60, 7543-7552
19. Guthrie, D. B.; Curran, D. P. Org. Lett. 2009, 11, 249-251
20. Shirakawa, S.; Liu, K.; Maruoka, K. J. Am. Chem. Soc. 2012, 134, 916-919
21. Pineschi, M.; Bertolini, F.; Crotti, P.; Macchia, F. Org. Lett. 2006, 8, 2627-2630
22. Rudolph, A.; Rackelmann, N.; Lautens, M. Angew. Chem., Int. Ed. 2007, 46, 1485-1488
23. Rudolph, A.; Rackelmann, N.; Turcotte-Savard, M.-O.; Lautens, M. J. Org. Chem. 2009, 74, 289-297
24. Yamada, K.; Kurokawa, T.; Tokuyama, H.; Fukuyama, T. J. Am. Chem. Soc. 2003, 125, 6630-6631
25. For a recent example describing organocatalytic asymmetric synthesis of related indolin-2-yl acetic acids, see: Miyaji, R.; Asano, K.; Matsubara, S. Org. Lett. 2013, 15, 3658-3661
26. Clerici, P.; Wennemers, H. Org. Biomol. Chem. 2012, 10, 110-113
27. Arakawa, Y.; Fritz, S. P.; Wennemers, H. J. Org. Chem. 2014, 79, 3937-3945
28. Bahlinger, A.; Fritz, S. P.; Wennemers, H. Angew. Chem., Int. Ed. 2014, 10.1002/acie.201310532
29. Chang, C.-F.; Huang, C.-Y.; Huang, Y.-C.; Lin, K.-Y.; Lee, Y.-J.; Wang, C.-J. Synth. Commun. 2010, 40, 3452-3466
30. Vakulya, B.; Varga, S.; Csampai, A.; Soos, T. Org. Lett. 2005, 7, 1967-1969
31. Li, B.-J.; Jiang, L.; Liu, M.; Chen, Y.-C.; Ding, L.-S.; Wu, Y. Synlett 2005, 603-606
32. Ye, J.; Dixon, D. J.; Hynes, P. S. Chem. Commun. 2005, 4481-4483
33. McCooey, S. H.; Connon, S. J. Angew. Chem., Int. Ed. 2005, 44, 6367-6370
34. For another example of undesired hydroxamic acid formation, see: Kimmel, K. L.; Weaver, J. D.; Lee, M.; Ellman, J. A. J. Am. Chem. Soc. 2012, 134, 11828-11828
35. 3 (2 equiv), see: Mattingly, P. G.; Miller, M. J. J. Org. Chem. 1980, 45, 410-415
36. Yang, B. H.; Buchwald, S. L. Org. Lett. 1999, 1, 35-37
37. Anderson, J. C.; Noble, A.; Tocher, D. A. J. Org. Chem. 2012, 77, 6703-6727
38. Marek, I.; Minko, Y.; Pasco, M.; Mejuch, T.; Gilboa, N.; Chechik, H.; Das, J. P. J. Am. Chem. Soc. 2014, 136, 2682-2694
39. Das, J. P.; Marek, I. Chem. Commun. 2011, 47, 4593-4623
40. The only previously described example relies on chiral resolution, see: Kost, A. N.; Romanova, N. N.; Budylin, V. A.; Grishina, G. V.; Potapov, V. M.; Bundel', Y. G.; Ben, A.; Vrubel', E.; Tyaglov, B. V. Chem. Heterocycl. Compd. 1983, 19, 638-641