α- and α′-Lithiation-Electrophile Trapping of N-Thiopivaloyl and N-tert-Butoxythiocarbonyl α-Substituted Azetidines: Rationalization of the Regiodivergence Using NMR and Computation

Journal of Organic Chemistry

Volumn 80, Issue 20, 2015, Pages 9838-9846

  Jackson, Kelvin E ^a   Mortimer, Claire L ^a   Odell, Barbara ^a   McKenna, Jeffrey M ^b   Claridge, Timothy D W ^a   Paton, Robert S ^a   Hodgson, David M ^a  

^a UNIVERSITY OF OXFORD   (United Kingdom)

^b NOVARTIS INSTITUTES FOR BIOMEDICAL RESEARCH   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

AZETIDINE DERIVATIVE; CARBONYL DERIVATIVE; ELECTROPHILE; METHYL GROUP; NITROGEN; THIOAMIDE; TOLUENE; THIOL DERIVATIVE;

ACCURACY; ARTICLE; CONFORMATION; CONJUGATION; LITHIATION; METHYLATION; NUCLEAR OVERHAUSER EFFECT; PROTON NUCLEAR MAGNETIC RESONANCE; QUANTITATIVE ANALYSIS; SOLVATION; SUBSTITUTION REACTION; SYNTHESIS; TEMPERATURE SENSITIVITY; CHEMICAL STRUCTURE; CHEMISTRY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; QUANTUM THEORY;

AZETIDINES; MAGNETIC RESONANCE SPECTROSCOPY; MOLECULAR STRUCTURE; QUANTUM THEORY; SULFHYDRYL COMPOUNDS;

EID: 84944930015     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/acs.joc.5b01804     Document Type: Article

References (38)

1. Mitchell, E. A.; Peschiulli, A.; Lefevre, N.; Meerpoel, L.; Maes, B. U. W. Chem.-Eur. J. 2012, 18, 10092-10142 10.1002/chem.201201539
2. Beak, P.; Lee, W. K. J. Org. Chem. 1993, 58, 1109-1117 10.1021/jo00057a024
3. Xiao, D.; Lavey, B. J.; Palani, A.; Wang, C.; Aslanian, R. G.; Kozlowski, J. A.; Shih, N.-Y.; McPhail, A. T.; Randolph, G. P.; Lachowicz, J. E.; Duffy, R. A. Tetrahedron Lett. 2005, 46, 7653-7656 10.1016/j.tetlet.2005.08.148
4. Sheikh, N. S.; Leonori, D.; Barker, G.; Firth, J. D.; Campos, K. R.; Meijer, A. J. H. M.; O'Brien, P.; Coldham, I. J. Am. Chem. Soc. 2012, 134, 5300-5308 10.1021/ja211398b
5. Beng, T. K.; Woo, J. S.; Gawley, R. E. J. Am. Chem. Soc. 2012, 134, 14764-14771 10.1021/ja306276w
6. Pandey, G.; Bagul, T. D.; Sahoo, A. K. J. Org. Chem. 1998, 63, 760-768 10.1021/jo971728+
7. Stuhlmann, F.; Kaufmann, D. E. J. Prakt. Chem. 1999, 341, 455-460 10.1002/(SICI)1521-3897(199907)341:5<455::AID-PRAC455>3.0.CO;2-2
8. Suga, S.; Watanabe, M.; Yoshida, J. J. Am. Chem. Soc. 2002, 124, 14824-14825 10.1021/ja028663z
9. Gross, K. M. B.; Beak, P. J. Am. Chem. Soc. 2001, 123, 315-321 10.1021/ja002662u
10. Gawley, R. E.; Connor, S. O.; Klein, R. In Science of Synthesis; Snieckus, V.; Majewski, M., Eds.; Thieme: Stuttgart, 2006; Vol. 8a, pp 677-757.
11. Singh, G. S.; D'hooghe, M.; De Kimpe, N. In Comprehensive Heterocyclic Chemistry III, 3 rd ed.; Stevens, C. V., Ed.; Elsevier: Oxford, 2008; Vol. 2, pp 1-110.
12. Brandi, A.; Cicchi, S.; Cordero, F. M. Chem. Rev. 2008, 108, 3988-4035 10.1021/cr800325e
13. Couty, F. In Science of Synthesis; Schaumann, E.; Enders, D., Eds.; Thieme: Stuttgart, 2009; Vol. 40a, pp 773-816.
14. Rousseau, G.; Robin, S. In Modern Heterocyclic Chemistry, 1 st ed.; Alzerez-Builla, J.; Vaquero, J. J.; Barluenga, J., Eds.; Wiley-VCH: Weinheim, 2011; Vol. 1, pp 163-268.
15. West, F. G.; Bott, T. M. Heterocycles 2012, 84, 223-264 10.3987/REV-11-SR(P)9
16. Hodgson, D. M.; Kloesges, J. Angew. Chem., Int. Ed. 2010, 49, 2900-2903 10.1002/anie.201000058
17. Hodgson, D. M.; Pearson, C. I.; Thompson, A. L. J. Org. Chem. 2013, 78, 1098-1106 10.1021/jo3025225
18. Hodgson, D. M.; Mortimer, C. L.; McKenna, J. M. Org. Lett. 2015, 17, 330-333 10.1021/ol503441d
19. Sippy, K. B.; Anderson, D. J.; Brunnelle, W. H.; Hutchins, C. W.; Schrimpf, M. R. Bioorg. Med. Chem. Lett. 2009, 19, 1682-1685 10.1016/j.bmcl.2009.01.099
20. Degennaro, L.; Zenzola, M.; Trinchera, P.; Carroccia, L.; Giovine, A.; Romanazzi, G.; Falcicchio, A.; Luisi, R. Chem. Commun. 2014, 50, 1698-1700 10.1039/c3cc48555b
21. Coldham, I.; Copley, R. C. B.; Haxell, T. F. N.; Howard, S. Org. Lett. 2001, 3, 3799-3801 10.1021/ol016818m
22. Ashweek, N. J.; Coldham, I.; Haxell, T. F. N.; Howard, S. Org. Biomol. Chem. 2003, 1, 1532-1544 10.1039/b301502e
23. Cesari, M.; D'Ilario, L.; Giglio, E.; Perego, G. Acta Crystallogr., Sect. B: Struct. Crystallogr. Cryst. Chem. 1975, B31, 49-55 10.1107/S0567740875002099
24. Nastopoulos, V.; Gikas, M.; Matsoukas, J.; Dideberg, O. Zeitschrift für Kristallographie 1992, 199, 149-155 10.1524/zkri.1992.199.1-2.149
25. Clayden, J. Organolithiums: Selectivity for Synthesis; Baldwin, J. E.; Williams, R. M., Eds.; Elsevier: Oxford, 2002.
26. All computations were performed using Gaussian09, revision D.01: Frisch, M. Gaussian09, revision D.01; Gaussian, Inc., Wallingford, CT, 2009. A full description of all methods used, together with a complete list of computational references, is given in the Supporting Information.
27. Paton, R. S.; Steinhardt, S. E.; Vanderwal, C. D.; Houk, K. N. J. Am. Chem. Soc. 2011, 133, 3895-3905 10.1021/ja107988b
28. Fogueri, U. R.; Kozuch, S.; Karton, A.; Martin, J. M. L. J. Phys. Chem. A 2013, 117, 2269-2277 10.1021/jp312644t
29. Atomic radii taken from: Bondi, A. J. Phys. Chem. 1964, 68, 441-451 10.1021/j100785a001
30. Johnson, E. R.; Keinan, S.; Mori-Sanchez, P.; Contreras-Garcia, J.; Cohen, A. J.; Yang, W. J. Am. Chem. Soc. 2010, 132, 6498-6506 10.1021/ja100936w
31. Contreras-Garcia, J.; Johnson, E. R.; Keinan, S.; Chaudret, R.; Piquemal, J.; Beratan, D. N.; Yang, W. J. Chem. Theory Comput. 2011, 7, 625-632 10.1021/ct100641a
32. Wiberg, K. B.; Rablen, P. R. J. Am. Chem. Soc. 1995, 117, 2201-2209 10.1021/ja00113a009
33. Wiberg, K. B.; Rush, D. J. J. Am. Chem. Soc. 2001, 123, 2038-2046 10.1021/ja003586y
34. Chang, D. L.; Feiten, H.-J.; Engesser, K.-H.; van Beilen, J. B.; Witholt, B.; Li, Z. Org. Lett. 2002, 4, 1859-1862 10.1021/ol025829s
35. Zhao, Y.; Truhlar, D. G. Theor. Chem. Acc. 2008, 120, 215-241 10.1007/s00214-007-0310-x
36. Hodgson, D. M.; Charlton, A.; Paton, R. S.; Thompson, A. S. J. Org. Chem. 2013, 78, 1508-1518 10.1021/jo3025972
37. Simon, L.; Paton, R. S. J. Org. Chem. 2015, 80, 2756-2766 10.1021/acs.joc.5b00063
38. Pangborn, A. B.; Giardello, M. A.; Grubbs, R. H.; Rosen, R. K.; Timmers, F. J. Organometallics 1996, 15, 1518-1520 10.1021/om9503712