Erratum: Asymmetric Synthesis of Highly Substituted β-Lactones through Oxidative Carbene Catalysis with LiCl as Cooperative Lewis Acid (Angew. Chem. Int. Ed. (2014) 53(DOI:10.1002/anie.201405200);Asymmetric synthesis of highly substituted β-lactones through oxidative carbene catalysis with LiCl as cooperative lewis acid

Angewandte Chemie - International Edition

Volumn 53, Issue 36, 2014, Pages 9622-9626

  Bera, Srikrishna ^a   Samanta, Ramesh C ^a   Daniliuc, Constantin G ^a   Studer, Armido ^a  

^a UNIVERSITY OF MÜNSTER   (Germany)

Author keywords

asymmetric synthesis; cooperative catalysis; N heterocyclic carbenes; organo catalysis; lactones

Indexed keywords

CATALYSIS; CHLORINE COMPOUNDS; ENANTIOSELECTIVITY; ESTERS; KETONES; SYNTHESIS (CHEMICAL);

ASYMMETRIC SYNTHESIS; C-C BOND FORMATION; C-O BOND FORMATION; COOPERATIVE CATALYSIS; DIASTEREO- AND ENANTIOSELECTIVITY; N-HETEROCYCLIC CARBENES; STEREOCENTERS; STEREOGENIC CENTERS;

LITHIUM COMPOUNDS;

CARBENE; CYCLOHEXANE DERIVATIVE; LACTONE; LEWIS ACID; LITHIUM CHLORIDE; METHANE; OXIDIZING AGENT;

ANALOGS AND DERIVATIVES; CATALYSIS; CHEMISTRY; OXIDATION REDUCTION REACTION; STEREOISOMERISM; SYNTHESIS;

CATALYSIS; CYCLOHEXANES; LACTONES; LEWIS ACIDS; LITHIUM CHLORIDE; METHANE; OXIDANTS; OXIDATION-REDUCTION; STEREOISOMERISM;

EID: 84906948370     PISSN: 14337851     EISSN: 15213773     Source Type: Journal    
DOI: 10.1002/anie.201409589     Document Type: Erratum

References (57)

1. T. Böttcher, S. A. Sieber, MedChemComm 2012, 3, 408.
2. E. K. Weibel, P. Hadvary, E. Hochuli, H. Lengsfeld, J. Antibiot. 1987, 40, 1081.
3. D.-Z. Liu, F. Wang, T.-G. Liao, J.-G. Tang, W. Steglich, H.-J. Zhu, J.-K. Liu, Org. Lett. 2006, 8, 5749.
4. R. H. Feling, G. O. Buchanan, T. J. Mincer, C. A. Kauffman, P. R. Jensen, W. Fenical, Angew. Chem. 2003, 115, 369
5. Angew. Chem. Int. Ed. 2003, 42, 355.
6. D. Enders, C. Grondal, M. R. Hüttl, Angew. Chem. 2007, 119, 1590
7. Angew. Chem. Int. Ed. 2007, 46, 1570
8. A. M. Walji, D. W. C. MacMillan, Synlett 2007, 1477
9. X. Yu, W. Wang, Org. Biomol. Chem. 2008, 6, 2037
10. J. Zhou, Chem. Asian J. 2010, 5, 422
11. A. Grossmann, D. Enders, Angew. Chem. 2012, 124, 320
12. Angew. Chem. Int. Ed. 2012, 51, 314.
13. D. Enders, O. Niemeier, A. Henseler, Chem. Rev. 2007, 107, 5606
14. N. Marion, S. Diez-Gonzalez, S. P. Nolan, Angew. Chem. 2007, 119, 3046
15. Angew. Chem. Int. Ed. 2007, 46, 2988
16. V. Nair, S. Vellalath, B. P. Babu, Chem. Soc. Rev. 2008, 37, 2691
17. J. L. Moore, T. Rovis, Top. Curr. Chem. 2009, 291, 77
18. V. Nair, R. S. Menon, A. T. Biju, C. R. Sinu, R. R. Paul, A. Jose, V. Sreekumar, Chem. Soc. Rev. 2011, 40, 5336
19. X. Bugaut, F. Glorius, Chem. Soc. Rev. 2012, 41, 3511
20. J. Douglas, G. Churchill, A. D. Smith, Synthesis 2012, 44, 2295
21. H. U. Vora, P. Wheeler, T. Rovis, Adv. Synth. Catal. 2012, 354, 1617
22. S. J. Ryan, L. Candish, D. W. Lupton, Chem. Soc. Rev. 2013, 42, 4906
23. K. Thai, E. Sanchez-Larios, M. Gravel, Comprehensive Enantioselective Organocatalysis (Ed.:, P. I. Dalko,), Wiley-VCH, Weinheim, 2013, p. 477
24. J. Mahatthananchai, J. W. Bode, Acc. Chem. Res. 2014, 47, 696.
25. M. Wadamoto, E. M. Phillips, T. E. Reynolds, K. A. Scheidt, J. Am. Chem. Soc. 2007, 129, 10098
26. E. M. Phillips, J. M. Roberts, K. A. Scheidt, Org. Lett. 2010, 12, 2830
27. D. T. Cohen, C. C. Eichman, E. M. Phillips, E. R. Zarefsky, K. A. Scheidt, Angew. Chem. 2012, 124, 7421
28. Angew. Chem. Int. Ed. 2012, 51, 7309
29. R. C. Johnston, D. T. Cohen, C. C. Eichman, K. A. Scheidt, P. H.-Y. Cheong, Chem. Sci. 2014, 5, 1974.
30. V. Nair, S. Vellalath, M. Poonoth, E. Suresh, J. Am. Chem. Soc. 2006, 128, 8736
31. P.-C. Chiang, J. Kaeobamrung, J. W. Bode, J. Am. Chem. Soc. 2007, 129, 3520
32. J. Kaeobamrung, J. W. Bode, Org. Lett. 2009, 11, 677.
33. C. E. I. Knappke, A. Imami, A. J. von Wangelin, ChemCatChem 2012, 4, 937
34. S. De Sarkar, A. Biswas, R. C. Samanta, A. Studer, Chem. Eur. J. 2013, 19, 4664.
35. S. J. Ryan, L. Candish, D. W. Lupton, J. Am. Chem. Soc. 2009, 131, 14176.
36. For the generation of acylazolium ions through reaction of a NHC with active esters, see:, Z. Fu, J. Xu, T. Zhu, W. W. Y. Leong, Y. R. Chi, Nat. Chem. 2013, 5, 835.
37. R. C. Samanta, B. Maji, S. De Sarkar, K. Bergander, R. Fröhlich, C. Mück-Lichtenfeld, H. Mayr, A. Studer, Angew. Chem. 2012, 124, 5325
38. Angew. Chem. Int. Ed. 2012, 51, 5234; See also
39. S. De Sarkar, A. Studer, Angew. Chem. 2010, 122, 9452-9455
40. Angew. Chem. Int. Ed. 2010, 49, 9266-9269
41. A. Biswas, S. De Sarkar, R. Fröhlich, A. Studer, Org. Lett. 2011, 13, 4966
42. A. Biswas, S. De Sarkar, L. Tebben, A. Studer, Chem. Commun. 2012, 48, 5190.
43. L. Candish, D. W. Lupton, J. Am. Chem. Soc. 2013, 135, 58.
44. G. Liu, M. E. Shirley, K. N. Van, R. L. McFarlin, D. Romo, Nat. Chem. 2013, 5, 1049.
45. S. De Sarkar, S. Grimme, A. Studer, J. Am. Chem. Soc. 2010, 132, 1190
46. S. De Sarkar, A. Studer, Org. Lett. 2010, 12, 1992.
47. J. R. Struble, J. W. Bode, Org. Synth. 2010, 87, 362.
48. I. Piel, M. Steinmetz, K. Hirano, R. Fröhlich, S. Grimme, F. Glorius, Angew. Chem. 2011, 123, 5087
49. Angew. Chem. Int. Ed. 2011, 50, 4983.
50. The crystallographic data for 4-aa (CCDC 996051), for the major isomer of compound 4-ad (CCDC 996053), for the major isomer of compound 4-ak (CCDC 996054), and for compound 7 (CCDC 996052) can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/data-request/ cif.
51. D. E. A. Raup, B. Cardinal-David, D. Holte, K. A. Scheidt, Nat. Chem. 2010, 2, 766
52. D. T. Cohen, K. A. Scheidt, Chem. Sci. 2012, 3, 53
53. J. Mo, X. Chen, Y. R. Chi, J. Am. Chem. Soc. 2012, 134, 8810
54. J. Dugal-Tessier, E. A. O'Brian, T. B. H. Schroeder, D. T. Cohen, K. A. Scheidt, Angew. Chem. 2012, 124, 5047
55. Angew. Chem. Int. Ed. 2012, 51, 4963
56. Y. Zhang, Y. Lu, W. Tang, T. Lu, D. Du, Org. Biomol. Chem. 2014, 12, 3009-3015.
57. S. J. Ryan, A. Stasch, M. N. Paddon-Row, D. W. Lupton, J. Org. Chem. 2012, 77, 1113.