Highly efficient synthesis of functionalized α-oxyketones: Via Weinreb amides homologation with α-oxygenated organolithiums

Chemical Communications

Volumn 52, Issue 48, 2016, Pages 7584-7587

  Pace, Vittorio ^a   Murgia, Irene ^a   Westermayer, Sophie ^a   Langer, Thierry ^a   Holzer, Wolfgang ^a  

^a UNIVERSITY OF VIENNA   (Austria)

Author keywords

[No Author keywords available]

Indexed keywords

AMIDE; KETONE DERIVATIVE; LITHIUM;

ALKYLATION; ARTICLE; ELECTROPHILICITY; LITHIATION; OXYGENATION; PRECURSOR; STEREOCHEMISTRY; SYNTHESIS;

EID: 84974660150     PISSN: 13597345     EISSN: 1364548X     Source Type: Journal    
DOI: 10.1039/c6cc03532a     Document Type: Article

References (67)

1. F. Colpaert S. Mangelinckx M. T. Rocchetti N. De Kimpe Org. Biomol. Chem. 2011 9 549
2. M. Sommelet Bull. Chem. Soc. Fr. 1907 377
3. D. D. Pratt J. Chem. Soc. 1923 745
4. H. R. Henze G. W. Benz G. L. Sutherland J. Am. Chem. Soc. 1949 71 2122
5. T. Eicher M. Wobido A. Speicher J. Prakt. Chem. 1996 338 706
6. B. Camuzat-Dedenis O. Provot H. Moskowitz J. Mayrargue Synthesis 1999 1558
7. M. Hamzaoui O. Provot B. Camuzat-Dedenis H. Moskowitz J. Mayrargue L. Cicéron F. Gay Tetrahedron Lett. 1998 39 4029
8. R. M. Moriarty O. Prakash M. P. Duncan R. K. Vaid H. A. Musallam J. Org. Chem. 1987 52 150
9. P. Mizar T. Wirth Angew. Chem., Int. Ed. 2014 53 5993
10. N. De Kimpe and R. Verhé, in The Chemistry of α-Haloketones, α-Haloaldehydes and α-Haloimines, ed., S. Patai, Wiley, Chichester, 1988
11. N. De Kimpe P. Sulmon L. Moens N. Schamp J. P. Declercq M. Van Meerssche J. Org. Chem. 1986 51 3839
12. N. de Kimpe W. de Cock C. Stevens Tetrahedron 1992 48 2739
13. N. De Kimpe N. Schamp Org. Prep. Proced. Int. 1979 11 115
14. J. Amani E. Sodagar G. A. Molander Org. Lett. 2016 18 732
15. S. Rozen E. Mishani M. Kol J. Am. Chem. Soc. 1992 114 7643
16. G. Zweifel A. Horng J. E. Plamondon J. Am. Chem. Soc. 1974 96 316
17. C. L. Stevens S. J. Dykstra J. Am. Chem. Soc. 1954 76 4402
18. M. Xu T.-T. Ren C.-Y. Li Org. Lett. 2012 14 4902
19. M. S. Newman P. F. Beal J. Am. Chem. Soc. 1950 72 5161
20. N. R. Candeias R. Paterna P. M. P. Gois Chem. Rev. 2016 116 2937
21. F. Arndt B. Eistert Ber. Dtsch. Chem. Ges. 1935 68 200
22. M. Regitz and G. Maas, Diazo Compounds-Properties and Synthesis, Academic Press, Orlando, 1986
23. A. Ford H. Miel A. Ring C. N. Slattery A. R. Maguire M. A. McKervey Chem. Rev. 2015 115 9981
24. G. Maas Angew. Chem., Int. Ed. 2009 48 8186
25. J. J. Li, Name Reactions for Homologation, Wiley, Hoboken, 2009
26. M. Braun, in The Chemistry of Organolithium Compounds, ed., Z. Rappoport, and, I. Marek, John Wiley and Sons, Chichester, 2004, vol. 1, p. 829
27. V. Capriati S. Florio Chem.-Eur. J. 2010 16 4152
28. V. Capriati, in Contemporary Carbene Chemistry, ed., R. A. Moss, and, M. P. Doyle, John Wiley & Sons, Hoboken, 2014, pp. 327-362
29. S. Molitor V. H. Gessner Synlett 2015 861
30. R. H. V. Nishimura V. E. Murie R. A. Soldi J. L. C. Lopes G. C. Clososki J. Braz. Chem. Soc. 2015 26 2175
31. V. Pace Aust. J. Chem. 2014 67 311
32. V. Pace W. Holzer G. Verniest A. R. Alcántara N. De Kimpe Adv. Synth. Catal. 2013 355 919
33. V. Pace L. Castoldi W. Holzer J. Org. Chem. 2013 78 7764
34. A. D. Mamuye L. Castoldi U. Azzena W. Holzer V. Pace Org. Biomol. Chem. 2015 13 1969
35. V. Pace A. Pelosi D. Antermite O. Rosati M. Curini W. Holzer Chem. Commun. 2016 52 2639
36. V. Pace L. Castoldi A. D. Mamuye T. Langer W. Holzer Adv. Synth. Catal. 2016 358 172
37. V. Pace L. Castoldi A. D. Mamuye W. Holzer Synthesis 2014 2897
38. V. Pace L. Castoldi W. Holzer Adv. Synth. Catal. 2014 356 1761
39. V. Pace L. Castoldi W. Holzer Chem. Commun. 2013 49 8383
40. J. Clayden, Organolithiums: Selectivity for Synthesis, Pergamon, Oxford, 2002
41. Lithium Compounds in Organic Synthesis From Fundamentals to Applications, ed., R. Luisi, and, V. Capriati, Wiley-VCH, Weinheim, 2014
42. U. Schöllkopf Angew. Chem., Int. Ed. Engl. 1970 9 763
43. J. F. Garst C. D. Smith J. Am. Chem. Soc. 1976 98 1526
44. G. Wittig L. Löhmann Justus Liebigs Ann. Chem. 1942 550 260
45. J. Barluenga F. J. Fañanás R. Sanz C. Marcos M. Trabada Org. Lett. 2002 4 1587
46. R. Velasco C. Feberero R. Sanz Org. Lett. 2015 17 4416
47. B. M. Trost G. K. Mikhail J. Am. Chem. Soc. 1987 109 4124
48. J. G. Montana N. Phillipson R. J. K. Taylor J. Chem. Soc., Chem. Commun. 1994 2289
49. U. Azzena and L. Pisano, in Lithium Compounds in Organic Synthesis, ed., R. Luisi, and, V. Capriati, Wiley-VCH, Weinheim, 2014, p. 351
50. A. Guijarro M. Yus Tetrahedron Lett. 1993 34 3487
51. A. Guijarro B. Mancheño J. Ortiz M. Yus Tetrahedron 1996 52 1643
52. M. Yus and F. Foubelo, in Handbook of Functionalized Organometallics, ed., P. Knochel, Wiley-VCH, Weinheim, 2005
53. C. Gómez S. Ruiz M. Yus Tetrahedron Lett. 1998 39 1397
54. C. Gómez S. Ruiz M. Yus Tetrahedron 1999 55 7017
55. U. Azzena S. Demartis M. G. Fiori G. Melloni L. Pisano Tetrahedron Lett. 1995 36 5641
56. U. Azzena M. Carraro C. Meloni I. Murgia L. Pisano M. Pittalis R. Luisi B. Musio L. Degennaro Tetrahedron: Asymmetry 2014 25 1550
57. S. Nahm S. M. Weinreb Tetrahedron Lett. 1981 22 3815
58. S. Balasubramaniam I. S. Aidhen Synthesis 2008 3707
59. V. Pace W. Holzer B. Olofsson Adv. Synth. Catal. 2014 356 3697
60. V. Pace W. Holzer Aust. J. Chem. 2013 66 507
61. V. Pace L. Castoldi A. R. Alcantara W. Holzer RSC Adv. 2013 3 10158
62. 3 and n -BuLi has been reported
63. N. Toda M. Ori K. Takami K. Tago H. Kogen Org. Lett. 2003 5 269
64. V. Pace Aust. J. Chem. 2012 65 301
65. V. Pace P. Hoyos L. Castoldi P. Domínguez de María A. R. Alcántara ChemSusChem 2012 5 1369
66. V. Pace L. Castoldi S. Monticelli S. Safranek A. Roller T. Langer W. Holzer Chem.-Eur. J. 2015 21 18966
67. K. Watanabe N. Yamagiwa Y. Torisawa Org. Process Res. Dev. 2007 11 251