Enantioselective Formal α-Methylation and α-Benzylation of Aldehydes by Means of Photo-organocatalysis

Angewandte Chemie - International Edition

Volumn 56, Issue 16, 2017, Pages 4447-4451

  Filippini, Giacomo ^b   Silvi, Mattia ^b   Melchiorre, Paolo ^a,b  

^a INSTITUCIÓ CATALANA DE RECERCA I ESTUDIS AVANÇATS ICREA   (Spain)

^b BARCELONA INSTITUTE OF SCIENCE AND TECHNOLOGY   (Spain)

Author keywords

enamines; organocatalysis; photochemistry; radicals; reaction mechanisms

Indexed keywords

ALDEHYDES; AMINES; CATALYSIS; ENANTIOSELECTIVITY; GROUND STATE; KETONES; PHOTOCHEMICAL REACTIONS; RATE CONSTANTS; STEREOCHEMISTRY;

CARBON-CENTERED RADICALS; ENAMINES; ORGANOCATALYSIS; RADICAL TRAPPING; RADICALS; REACTION MECHANISM; REDUCING CONDITIONS; STEREOCHEMICAL CONTROL;

ALKYLATION;

EID: 85016029088     PISSN: 14337851     EISSN: 15213773     Source Type: Journal    
DOI: 10.1002/anie.201612045     Document Type: Article

References (53)

1. Modern Carbonyl Chemistry (Ed.; J. Otera), Wiley-WCH, Weinheim, 2000;
2. Principles of Asymmetric Synthesis, 2nd ed. (Eds. R. E. Gawley, J. Aubé), Elsevier, Amsterdam, 2012, chap. 3.
3. D. Enders, H. Eichenauer, Tetrahedron Lett. 1977, 18, 191–194;
4. D. Enders, H. Eichenauer, Chem. Ber. 1979, 112, 2933–2960;
5. R. Schmierer, G. Grotemeier, G. Helmchen, A. Selim, Angew. Chem. Int. Ed. Engl. 1981, 20, 207–208;
6. Angew. Chem. 1981, 93, 209–211;
7. D. A. Evans, M. D. Ennis, D. J. Mathre, J. Am. Chem. Soc. 1982, 104, 1737–1739;
8. W. Oppolzer, R. Moretti, S. Thomi, Tetrahedron Lett. 1989, 30, 5603–5606.
9. M. Imai, A. Hagihara, H. Kawasaki, K. Manabe, K. Koga, J. Am. Chem. Soc. 1994, 116, 8829–8830;
10. A. G. Doyle, E. N. Jacobsen, J. Am. Chem. Soc. 2005, 127, 62–63;
11. C. Fischer, G. C. Fu, J. Am. Chem. Soc. 2005, 127, 4594–4595.
12. P. Melchiorre, Angew. Chem. Int. Ed. 2009, 48, 1360–1363;
13. Angew. Chem. 2009, 121, 1386–1389.
14. T. Hashimoto, K. Maruoka, Chem. Rev. 2007, 107, 5656–5682.
15. S. Mukherjee, J. W. Yang, S. Hoffmann, B. List, Chem. Rev. 2007, 107, 5471–5569.
16. N2-type alkylation, see:
17. N. Vignola, B. List, J. Am. Chem. Soc. 2004, 126, 450–451;
18. D. Enders, C. Wang, J. W. Bats, Angew. Chem. Int. Ed. 2008, 47, 7539–7542;
19. Angew. Chem. 2008, 120, 7649–7653.
20. For selected examples, see:
21. R. R. Shaikh, A. Mazzanti, M. Petrini, G. Bartoli, P. Melchiorre, Angew. Chem. Int. Ed. 2008, 47, 8707–8710;
22. Angew. Chem. 2008, 120, 8835–8838;
23. P. G. Cozzi, F. Benfatti, L. Zoli, Angew. Chem. Int. Ed. 2009, 48, 1313–1316;
24. Angew. Chem. 2009, 121, 1339–1342;
25. A. R. Brown, W.-H. Kuo, E. N. Jacobsen, J. Am. Chem. Soc. 2010, 132, 9286–9288.
26. D. Nicewicz, D. W. C. MacMillan, Science 2008, 322, 77–80;
27. H.-W. Shih, M. N. VanderWal, R. L. Grange, D. W. C. MacMillan, J. Am. Chem. Soc. 2010, 132, 13600–13603. For organocatalytic methods, in the absence of any external photoredox catalyst, see:
28. E. Arceo, I. D. Jurberg, A. Álvarez-Fernández, P. Melchiorre, Nat. Chem. 2013, 5, 750–756.
29. The previous formal α-methylation of aldehydes did not use an organic halide but 1,3-benzodithiolylium tetrafluoroborate, which served as a carbocation precursor. See: A. Gualandi, E. Emer, M. Guiteras Capdevila, P. G. Cozzi, Angew. Chem. Int. Ed. 2011, 50, 7842–7846;
30. Angew. Chem. 2011, 123, 7988–7992.
31. B. List, I. Čorić, O. O. Grygorenko, P. S. J. Kaib, I. Komarov, A. Lee, M. Leutzsch, S. Chandra Pan, A. V. Tymtsunik, M. van Gemmeren, Angew. Chem. Int. Ed. 2014, 53, 282–285;
32. Angew. Chem. 2014, 126, 286–289.
33. H. Schönherr, T. Cernak, Angew. Chem. Int. Ed. 2013, 52, 12256–12267;
34. Angew. Chem. 2013, 125, 12480–12492;
35. C. S. Leung, S. S. F. Leung, J. Tirado-Rives, W. L. Jorgensen, J. Med. Chem. 2012, 55, 4489–4500.
36. M. Silvi, E. Arceo, I. D. Jurberg, C. Cassani, P. Melchiorre, J. Am. Chem. Soc. 2015, 137, 6120–6123;
37. A. Bahamonde, P. Melchiorre, J. Am. Chem. Soc. 2016, 138, 8019–8030.
38. J. Yoshida, K. Kataoka, R. Horcajada, A. Nagaki, Chem. Rev. 2008, 108, 2265–2299;
39. E. L. Tyson, E. P. Farney, T. P. Yoon, Org. Lett. 2012, 14, 1110–1113;
40. J. W. Beatty, J. J. Douglas, K. P. Cole, C. R. Stephenson, Nat. Commun. 2015, 6, 7919.
41. For reports on the generation of phenylsulfonyl methyl radicals, see:
42. M. Masnyk, Tetrahedron Lett. 1991, 32, 3259–3262;
43. J. Gui, Q. Zhou, C. Pan, Y. Yabe, A. C. Burns, M. R. Collins, M. A. Ornelas, Y. Ishihara, P. S. Baran, J. Am. Chem. Soc. 2014, 136, 4853–4856;
44. F. Liu, P. Li, J. Org. Chem. 2016, 81, 6972–6979.
45. B. S. Donslund, T. K. Johansen, P. H. Poulsen, K. S. Halskov, K. A. Jørgensen, Angew. Chem. Int. Ed. 2015, 54, 13860–13874;
46. Angew. Chem. 2015, 127, 14066–14081.
47. D. P. Curran, C.-T. Chang, Tetrahedron Lett. 1990, 31, 933–936;
48. A. Studer, D. P. Curran, Angew. Chem. Int. Ed. 2016, 55, 58–102;
49. Angew. Chem. 2016, 128, 58–106.
50. G. H. Jeffery, J. Bassett, J. Mendham, R. C. Denney, Vogel's Quantitative Chemical Analysis, 5th ed., Longman Scientific & Technical, Harlow Essex, 1989;
51. S. Ono, S. Tsuchihashi, T. Kuge, J. Am. Chem. Soc. 1953, 75, 3601–3602.
52. J. Lalevée, X. Allonas, J. P. Fouassier, Chem. Phys. Lett. 2008, 454, 415–418.
53. T. Pintauer, K. Matyjaszewski, Encyclopedia of Radicals, Vol. 4, Wiley, Hoboken, 2012, p. 1851.