Rotational isomers of N-methyl-N-arylacetamides and their derived enolates: Implications for asymmetric Hartwig oxindole cyclizations

Journal of Organic Chemistry

Volumn 78, Issue 8, 2013, Pages 4083-4089

  Mandel, Jérémie ^a   Pan, Xiaohong ^a   Hay, E Ben ^a   Geib, Steven J ^a   Wilcox, Craig S ^a   Curran, Dennis P ^a  

^a UNIVERSITY OF PITTSBURGH   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ATROPISOMERS; BASIC CONDITIONS; CYCLIZATIONS; FLASH CHROMATOGRAPHY; INTERCONVERSIONS; ROTATION BARRIERS; STEREOCENTERS; THERMAL CONDITION;

OLEFINS;

CYCLIZATION;

ACETAMIDE DERIVATIVE; ALKENE; CARBON; ENOLATE; FUNCTIONAL GROUP; METHYL GROUP; N (2 BROMO 4,6 DIMETHYLPHENYL) N METHYL 2 PHENYLPROPANAMIDE; NITROGEN; OXINDOLE; PROPIONAMIDE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; CHROMATOGRAPHY; CONTROLLED STUDY; CYCLIZATION; ENANTIOMER; EPIMERIZATION; HARTWIG CYCLIZATION; ISOMER; ISOMERISM; REDUCTION;

BENZENEACETAMIDES; CYCLIZATION; INDOLES; PHENYLPROPIONATES; STEREOISOMERISM;

EID: 84876532544     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo400385t     Document Type: Article

References (60)

1. Stewart, W. E.; Siddall, T. H. Chem. Rev. 1970, 70, 517-551
2. Oki, M.; Allinger, N. L.; Eliel, E.; Wilen, S. H. Topics in Stereochemistry; Wiley-Interscience: New York, 1983; Vol. 14, pp 1-81.
3. Gallo, R.; Roussel, C.; Berg, U. Adv. Hetercycl. Chem 1988, 43, 174-299
4. Eliel, E. L.; Wilen, S. Stereochemistry of Organic Compunds; Wiley-Interscience: New York, 1994.
5. Wolf, C. Dynamic Stereochemistry of Organic Compounds; RSC Publishing: Cambridge, 2008.
6. 2-alkenyl bonds: Clark, A. J.; Curran, D. P.; Geden, J. V.; James, N.; Wilson, P. J. Org. Chem. 2011, 76, 4546-4551
7. LaPlante, S. R.; D. Fader, L.; Fandrick, K. R.; Fandrick, D. R.; Hucke, O.; Kemper, R.; Miller, S. P. F.; Edwards, P. J. J. Med. Chem. 2011, 54, 7005-7022
8. Wilcox, C. S.; Bhayana, B. Angew. Chem. 2007, 46, 6833-6836
9. Wilcox, C. S.; Paliwal, S.; Kim, E. J. Am. Chem. Soc. 1998, 120, 11192-11193
10. Curran, D. P.; Qi, H.; Geib, S. J.; DeMello, N. C. J. Am. Chem. Soc. 1994, 116, 3131-3132
11. Guthrie, D. B.; Geib, S. J.; Curran, D. P. J. Am. Chem. Soc. 2009, 131, 15492-15500
12. Petit, M.; Geib, S. J.; Curran, D. P. Tetrahedron 2004, 60, 7543-7552
13. Curran, D. P.; Chen, C. H. T.; Geib, S. J.; Lapierre, A. J. B. Tetrahedron 2004, 60, 4413-4424
14. Curran, D. P.; Liu, W. D.; Chen, C. H.-T. J. Am. Chem. Soc. 1999, 121, 11012-11013
15. Ohnishi, Y.; Sakai, M.; Nakao, S.; Kitagawa, O. Org. Lett. 2011, 13, 2840-2843
16. Kitagawa, O.; Yoshikawa, M.; Tanabe, H.; Morita, T.; Takahashi, M.; Dobashi, Y.; Taguchi, T. J. Am. Chem. Soc. 2006, 128, 12923-12931
17. Kitagawa, O.; Takahashi, M.; Yoshikawa, M.; Taguchi, T. J. Am. Chem. Soc. 2005, 3676-3677
18. Hughes, A. D.; Price, D. A.; Simpkins, N. S. J. Chem. Soc., Perkin Trans. 1 1999, 1295-1304
19. Hughes, A. D.; Price, D. A.; Shishkin, O.; Simpkins, N. S. Tetrahedron Lett. 1996, 37, 7607-7110
20. Guthrie, D. B.; Curran, D. P. Org. Lett. 2009, 11, 249-251
21. Lapierre, A. J. B.; Geib, S. J.; Curran, D. P. J. Am. Chem. Soc. 2007, 129, 494-495
22. Dounay, A. B.; Overman, L. E. Chem. Rev. 2003, 103, 2945-2963
23. Ashimori, A.; Bachand, B.; Calter, M. A.; Govek, S. P.; Overman, L. E.; Poon, D. J. J. Am. Chem. Soc. 1998, 120, 6488-6499
24. Overman, L. E.; Poon, D. J. Angew. Chem., Int. Ed. Engl. 1997, 36, 518-521
25. Curran, D. P.; Hale, G. R.; Geib, S. J.; Balog, A.; Cass, Q. B.; Degani, A. L. G.; Hernandes, M. Z.; Freitas, L. C. G. Tetrahedron: Asymmetry 1997, 8, 3955-3975
26. Saito, S.; Toriumi, Y.; Tomioka, N.; Itai, A. J. Org. Chem. 1995, 60, 4715-4720
27. Itai, A.; Toriumi, Y.; Saito, S.; Kagechika, H.; Shudo, K. J. Am. Chem. Soc. 1992, 114, 10649-10650
28. Lee, S.; Hartwig, J. F. J. Org. Chem. 2001, 66, 3402-3415
29. Liu, L.; Ishida, N.; Ashida, S.; Murakami, M. Org. Lett. 2011, 13, 1666-1669
30. Jia, Y.-X.; Katayev, D.; Bernardinelli, G.; Seidel, T. M.; Kündig, E. P. Chem.-Eur. J. 2010, 16, 6300-6309
31. Würtz, S.; Lohre, C.; Fröhlich, R.; Bergander, K.; Glorius, F. J. Am. Chem. Soc. 2009, 131, 8344-8345
32. Arao, T.; Kondo, K.; Aoyama, T. Tetrahedron Lett. 2006, 47, 1417-1420
33. Trillo, R. B.; Leven, M.; Neudörfl, J. M.; Goldfuss, B. Adv. Synth. Catal. 2012, 354, 1451-1465
34. Pan, X. Ph.D. Thesis, University of Pittsburgh, 2012, http://etd.library.pitt.edu/ETD/available/etd-05282011-005856/.
35. Honda, T.; Namiki, H.; Satoh, F. Org. Lett. 2001, 3, 631
36. MacKay, J. A.; Bishop, R. L.; Rawal, V. H. Org. Lett. 2005, 7, 3421
37. Hillgren, J. M.; Marsden, S. P. J. Org. Chem. 2008, 73, 6459
38. Solé., D.; Serrano, O. J. Org. Chem. 2008, 73, 9372
39. Marsden, S. P.; Watson, E. L.; Raw, S. A. Org. Lett. 2008, 10, 2905
40. Durbin, M. J.; Willis, M. C. Org. Lett. 2008, 10, 1413
41. Solé, D.; Serrano, O. J. Org. Chem. 2008, 73, 2476
42. Satyanarayana, G.; Maier, M. E. Tetrahedron 2008, 64, 356
43. Watson, E. L.; Marsden, S. P.; Raw, S. A. Tetrahedron Lett. 2009, 50, 3318
44. Ackermann, L.; Vicente, R.; Hofmann, N. Org. Lett. 2009, 11, 4274
45. Pan, X.; Wilcox, C. S. J. Org. Chem. 2010, 75, 6445-6451
46. Zhao, H. W.; Hsu, D. C.; Carlier, P. R. Synthesis 2005, 1-16
47. Kawabata, T.; Fuji, K. Top. Stereochem. 2003, 23, 175-205
48. Cozzi, F.; Siegel, J. S. Org. Biomol. Chem. 2005, 3, 4296-4298
49. Bruch, A.; Ambrosius, A.; Fröhlich, R.; Studer, A.; Guthrie, D. B.; Zhang, H.; Curran, D. P. J. Am. Chem. Soc. 2010, 132, 11452-11454
50. Pirkle, W. H.; Welch, C. J.; Zych, A. J. J. Chrom. A 1993, 648, 101-109
51. Clayden, J.; Pink, J. H. Angew. Chem., Int. Ed. Engl. 1998, 37, 1937-1939
52. Mekelburger, H. B.; Wilcox, C. S. In Comprehensive Organic Synthesis; Trost, B. M.; Fleming, I., Eds.; Pergamon Press: Oxford, 1991; Vol. 2, p 99.
53. Deetz, M. J.; Forbes, C. C.; Jonas, M.; Malerich, J. P.; Smith, B. D.; Wiest, O. J. Org. Chem. 2002, 67, 3949-3952
54. Smith, B. D.; Goodenough-Lashua, D. M.; D'Souza, C. J. E.; Norton, K. J.; Schmidt, L. M.; Tung, J. C. Tetrahedron Lett. 2004, 45, 2747-2749
55. Julia, S.; Ginebreda, A.; Sala, P.; Sancho, M.; Annunziata, R.; Cozzi, F. Org. Mag. Res. 1983, 21, 573-575
56. Adler, T.; Bonjoch, J.; Clayden, J.; Font-Bardía, M.; Pickworth, M.; Solans, X.; Solé, D.; Vallverdú, L. Org. Biomol. Chem. 2005, 3, 3173-3183
57. For an example of p K a-dependent cross-conjugation effects on rotation barriers of heteroaryl amide C-C bonds, see: Welch, C. J.; Biba, M.; Pye, P.; Angelaud, R.; Egbertson, M. J. Chromatogr. B 2008, 875, 118-121
58. Suzumura, N.; Kageyama, M.; Kamimura, D.; Inagaki, T.; Dobashi, Y.; Hasegawa, H.; Fukaya, H.; Kitagawa, O. Tetrahedron Lett. 2012, 53, 4332-4336
59. Seebach, D.; Maetzke, T.; Petter, W.; Kloetzer, B.; Plattner, D. A. J. Am. Chem. Soc. 1991, 113, 1781-1786
60. Ates, A.; Curran, D. P. J. Am. Chem. Soc. 2001, 123, 5130-5131