Direct construction of quaternary carbons from tertiary alcohols via photoredox-catalyzed fragmentation of tert-alkyl N-phthalimidoyl oxalates

Journal of the American Chemical Society

Volumn 135, Issue 41, 2013, Pages 15342-15345

  Lackner, Gregory L ^a   Quasdorf, Kyle W ^a   Overman, Larry E ^a  

^a UNIVERSITY OF CALIFORNIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ELECTRON-DEFICIENT; QUATERNARY CARBON; TERTIARY ALCOHOLS; VISIBLE LIGHT;

SYNTHESIS (CHEMICAL);

CHEMISTRY;

ALCOHOL; ALKENE; CARBON; OXALIC ACID; TERT ALKYL N PHTHALIMIDOYL OXALATE; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; OXIDATION REDUCTION REACTION;

ALCOHOLS; ALKENES; CARBON; CATALYSIS; ELECTRONS; LIGHT; OXALATES; OXIDATION-REDUCTION; PHOTOCHEMICAL PROCESSES; PHTHALIMIDES; STEREOISOMERISM;

EID: 84886899607     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja408971t     Document Type: Article

References (27)

1. Damm, W.; Giese, B.; Hartung, J.; Hasskerl, T.; Houk, K. N.; Hüter; Zipse, H. J. Am. Chem. Soc. 1992, 114, 4067
2. Arnaud, R.; Postlethwaite, H.; Barone, V. J. Phys. Chem. 1994, 98, 5913
3. Giese, B. Angew. Chem., Int. Ed. 1983, 22, 753
4. Beckwith, A. L.; Poole, J. S. J. Am. Chem. Soc. 2002, 124, 9489
5. Hayen, A.; Koch, R.; Saak, W.; Haase, D.; Metzger, J. O. J. Am. Chem. Soc. 2000, 122, 12458
6. Renaud, P.; Sibi, M. P. Radicals in Organic Synthesis, Vol. 2; Wiley-VCH: Weinheim, 2001.
7. Zard, S. Z. Radical Reactions in Organic Synthesis; Oxford: New York, 2003.
8. Srikanth, G. S. C.; Castle, S. L. Tetrahedron 2005, 61, 10377
9. Rowlands, G. J. Tetrahedron 2009, 65, 8603
10. Barton, D. H. R.; Sas, W. Tetrahedron 1990, 46, 3419
11. Quaternary Stereocenters-Challenges and Solutions for Organic Synthesis; Christoffers, J.; Baro, A., Eds.; Wiley-VCH: Weinheim, 2005.
12. Schnermann, M. J.; Overman, L. E. Angew. Chem., Int. Ed. 2012, 51, 9576
13. Furst, L.; Narayanam, J. M. R.; Stephenson, C. R. J. Angew. Chem., Int. Ed. 2011, 50, 9655
14. For the pioneering development of N -(acyloxy)phthalimides for forming carbon radicals, see: Okada, K.; Okamoto, K.; Morita, N.; Okubo, K.; Oda, M. J. Am. Chem. Soc. 1991, 113, 9401
15. Tucker, J. W.; Stephenson, C. R. J. J. Org. Chem. 2012, 77, 1617
16. Prier, C. K.; Rankic, D. A.; MacMillan, D. W. C. Chem. Rev. 2013, 113, 5322
17. Barton, D. H. R.; Crich, D. Tetrahedron Lett. 1985, 26, 757
18. Barton, D. H. R.; Crich, D.; Kretzschmar, G. J. Chem. Soc., Perkin Trans. 1 1986, 39
19. Elimination is a serious complication;(10b) see also: Aggarwal, V. K.; Angelaud, R.; Bihan, D.; Blackburn, P.; Fieldhouse, R.; Fonquerna, S. J.; Ford, G. D.; Hynd, G.; Jones, E.; Jones, R. V. H.; Jubault, P.; Palmer, M. J.; Ratcliffe, P. D.; Adams, H. J. Chem. Soc., Perkin Trans. 1 2001, 2604
20. McCombie, S. W.; Motherwell, W. B.; Tozer, M. J. Org. React. 2012, 77, 161
21. Togo, H.; Fujii, M.; Yokoyama, M. Bull. Chem. Soc. Jpn. 1991, 64, 57
22. Togo, H.; Matsubayashi, S.; Yamazaki, O.; Yokoyama, M. J. Org. Chem. 2000, 65, 2816
23. Blazejewski, J.-C; Diter, P.; Warchol, T.; Wakselman, C. Tetrahedron Lett. 2001, 42, 859
24. Sunazuka, T.; Yoshida, K.; Kojima, N.; Shirahata, T.; Hirose, T.; Handa, M.; Yamamoto, D.; Harigaya, Y.; Kuwajima, I.; Omura, S. Tetrahedron Lett. 2005, 46, 1459
25. Togo, H.; Yokoyama, M. Heterocycles 1990, 31, 437
26. Morikawa, T.; Washio, Y.; Harada, S.; Hanai, R.; Kayashita, T.; Nemoto, H.; Shiro, M.; Taguchi, T. J. Chem. Soc., Perkin Trans. 1 1995, 271
27. Simakov, P. A.; Martinez, F. N.; Horner, J. H.; Newcomb, M. J. Org. Chem. 1998, 63, 1226