Detour and direct induction of methyl-containing chiral centers via catalytic C-H or C-C bond formation

Synthesis

Volumn 44, Issue 10, 2012, Pages 1427-1452

  Endo, Kohei ^a,b   Shibata, Takanori ^c  

^a KANAZAWA UNIVERSITY   (Japan)

^b JAPAN SCIENCE AND TECHNOLOGY AGENCY   (Japan)

^c WASEDA UNIVERSITY   (Japan)

Author keywords

asymmetric catalysis; asymmetric synthesis; chirality; methylation; natural products

Indexed keywords

ASYMMETRIC CATALYSIS; ASYMMETRIC INDUCTION; ASYMMETRIC SYNTHESIS; BIOLOGICALLY ACTIVE COMPOUNDS; C-C BOND FORMATION; C-H FUNCTIONALIZATION; CHIRAL CENTERS; CONJUGATE ADDITION; CROSS COUPLING REACTIONS; DIELS-ALDER REACTION; DIRECT APPROACH; ENZYMATIC TRANSFORMATION; HYDROBORATION; METHYL GROUP; NATURAL PRODUCTS; RING OPENING REACTION; SUZUKI-MIYAURA CROSS-COUPLING; TRIFLUOROMETHYLATION;

ALKYLATION; BIOACTIVITY; CHIRALITY; FRIEDEL-CRAFTS REACTION; FUNCTIONAL GROUPS; HYDROFORMYLATION; METHYLATION;

STEREOCHEMISTRY;

ALUMINUM DERIVATIVE; DIMETHYLZINC; GRIGNARD REAGENT; LITHIUM DERIVATIVE; MAGNESIUM DERIVATIVE; METHYLLITHIUM; METHYLMAGNESIUM; NICKEL; NIOBIUM; ORGANOALUMINUM REAGENT; ORGANOBORON REAGENT; ORGANOZINC REAGENT; PALLADIUM; REAGENT; TRIMETHYLALUMINUM; UNCLASSIFIED DRUG; ZINC DERIVATIVE;

ADDITION REACTION; ALKYLATION; BIOTRANSFORMATION; CARBOMETALLATION; CATALYSIS; CATALYST; CHEMICAL BINDING; CHEMICAL MODIFICATION; CHEMICAL STRUCTURE; CHIRALITY; DIELS ALDER REACTION; FRIEDEL CRAFTS REACTION; HYDROBORATION; HYDROFORMYLATION; HYDROGEN BOND; HYDROGENATION; METALLATION; METHYLATION; REVIEW; RING OPENING; STRUCTURE ANALYSIS; SUZUKI MIYAURA REACTION; TRIFLUOROMETHYLATION;

EID: 84859765857     PISSN: 00397881     EISSN: 1437210X     Source Type: Journal    
DOI: 10.1055/s-0031-1290869     Document Type: Review

References (81)

1. Review: Hall M, Bommarius AS. Chem. Rev.: 2011; 111 4088
2. Friest JA, Maezato Y, Broussy S, Blum P, Berkowitz DB. J. Am. Chem. Soc.: 2010; 132 5930
3. Paetzold J, Bäckvall JE. J. Am. Chem. Soc.: 2005; 127 17620
4. Mazuela J, Verendel JJ, Coll M, Schäffner B, Börner A, Andersson PG, Pmies O, Diguez M. J. Am. Chem. Soc.: 2009; 131 12344
5. Mazuela J, Norrby P.-O, Andersson PG, Pmies O, Diguez M. J. Am. Chem. Soc.: 2011; 133 13634
6. Zhao J, Burgess K. J. Am. Chem. Soc.: 2009; 131 13236
7. Benhaim C, Bouchard L, Pelletier G, Sellstedt J, Kristofova L, Daigneault S. Org. Lett.: 2010; 12 2008
8. Hughes G, Kimura M, Buchwald SL. J. Am. Chem. Soc.: 2003; 125 11253
9. Lipshutz BH, Servesko JM, Taft BR. J. Am. Chem. Soc.: 2004; 126 8352
10. Crudden CM, Hleba YB, Chen AC. J. Am. Chem. Soc.: 2004; 126 9200
11. Moteki SA, Wu D, Chandra KL, Reddy DS, Takacs JM. Org. Lett.: 2006; 8 3097
12. Chea H, Sim H.-S, Yun J. Adv. Synth. Catal.: 2009; 351 855
13. Sandrock DL, Jean-Grard L, Chen C.-y, Dreher SD, Molander GA. J. Am. Chem. Soc.: 2010; 132 17108
14. Yan Y, Zhang X. J. Am. Chem. Soc.: 2006; 128 7198
15. Robert T, Abiri Z, Wassenaar J, Sandee AJ, Romanski S, Neudörfl J.-M, Schmalz H.-G, Reek JN. H. Organometallics: 2010; 29 478
16. McDonald RI, Wong GW, Neupane RP, Stahl SS, Landis CR. J. Am. Chem. Soc.: 2010; 132 14027
17. Worthy AD, Joe CL, Lightburn TE, Tan KL. J. Am. Chem. Soc.: 2010; 132 14757
18. Wang X, Buchwald SL. J. Am. Chem. Soc.: 2011; 133 19080
19. Lu Z, Wilsily A, Fu GC. J. Am. Chem. Soc.: 2011; 133 8154
20. Zultanski SL, Fu GC. J. Am. Chem. Soc.: 2011; 133 15362
21. Lundin PM, Fu GC. J. Am. Chem. Soc.: 2010; 132 11027
22. Lou S, Fu GC. J. Am. Chem. Soc.: 2010; 132 5010
23. Lou S, Fu GC. J. Am. Chem. Soc.: 2010; 132 1264
24. Smith SW, Fu GC. J. Am. Chem. Soc.: 2008; 130 12645
25. Saito B, Fu GC. J. Am. Chem. Soc.: 2008; 130 6694
26. Dai X, Strotman NA, Fu GC. J. Am. Chem. Soc.: 2008; 130 3302
27. Son S, Fu GC. J. Am. Chem. Soc.: 2008; 130 2756
28. Zhang P, Le H, Kyne RE, Morken JP. J. Am. Chem. Soc.: 2011; 133 9716
29. Brozek LA, Ardolino MJ, Morken JP. J. Am. Chem. Soc.: 2011; 133 16778
30. Lpez F, Harutyunyan SR, Minnaard AJ, Feringa BL. J. Am. Chem. Soc.: 2004; 126 12784
31. Lpez F, Harutyunyan SR, Meetsma A, Minnaard AJ, Feringa BL. Angew. Chem. Int. Ed.: 2005; 44 2752
32. Lee S, MacMillan DW. C. J. Am. Chem. Soc.: 2007; 129 15438
33. Reiter M, Torssell S, Lee S, MacMillan DW. C. Chem. Sci.: 2010; 1 37
34. Shintani R, Hayashi T. Org. Lett.: 2011; 13 350
35. d'Augustin M, Palais L, Alexakis A. Angew. Chem. Int. Ed.: 2005; 44 1376
36. Hawner C, Li K, Cirriez V, Alexakis A. Angew. Chem. Int. Ed.: 2008; 47 8211
37. Hawner C, Müller D, Gremaud L, Felouat A, Woodward S, Alexakis A. Angew. Chem. Int. Ed.: 2010; 49 7769
38. May TL, Dabrowski JA, Hoveyda AH. J. Am. Chem. Soc.: 2011; 133 736
39. Shintani R, Takatsu K, Takeda M, Hayashi T. Angew. Chem. Int. Ed.: 2011; 50 8656
40. Ohmiya H, Makida Y, Li D, Tanabe M, Sawamura M. J. Am. Chem. Soc.: 2009; 132 879
41. Akiyama K, Gao F, Hoveyda AH. Angew. Chem. Int. Ed.: 2010; 49 419
42. Gao F, McGrath KP, Lee Y, Hoveyda AH. J. Am. Chem. Soc.: 2010; 132 14315
43. Gao F, Lee Y, Mandai K, Hoveyda AH. Angew. Chem. Int. Ed.: 2010; 49 8370
44. Dabrowski JA, Gao F, Hoveyda AH. J. Am. Chem. Soc.: 2011; 133 4778
45. Kuwano R, Uchida K.-i, Ito Y. Org. Lett.: 2003; 5 2177
46. For other examples of allylation reactions, see: Lu Z, Ma S. Angew. Chem. Int. Ed.: 2008; 47 258
47. Trost BM, Zhang Y. J. Am. Chem. Soc.: 2006; 128 4590
48. Trost BM, Quancard J. J. Am. Chem. Soc.: 2006; 128 6314
49. Kimura M, Futamata M, Mukai R, Tamaru Y. J. Am. Chem. Soc.: 2005; 127 4592
50. Behenna DC, Stoltz BM. J. Am. Chem. Soc.: 2004; 126 15044
51. Trost BM, Xu J. J. Am. Chem. Soc.: 2005; 127 2846
52. Mohr JT, Behenna DC, Harned AM, Stoltz BM. Angew. Chem. Int. Ed.: 2005; 44 6924
53. McFadden RM, Stoltz BM. J. Am. Chem. Soc.: 2006; 128 7738
54. Petrova KV, Mohr JT, Stoltz BM. Org. Lett.: 2009; 11 293
55. Day JJ, McFadden RM, Virgil SC, Kolding H, Alleva JL, Stoltz BM. Angew. Chem. Int. Ed.: 2011; 50 6814
56. Ooi T, Takeuchi M, Kato D, Uematsu Y, Tayama E, Sakai D, Maruoka K. J. Am. Chem. Soc.: 2005; 127 5073
57. Hong S, Lee J, Kim M, Park Y, Park C, Kim M.-h, Jew S.-s, Park H.-g. J. Am. Chem. Soc.: 2011; 133 4924
58. Spielvogel DJ, Buchwald SL. J. Am. Chem. Soc.: 2002; 124 3500
59. Liao X, Stanley LM, Hartwig JF. J. Am. Chem. Soc.: 2011; 133 2088
60. Zhang A, RajanBabu TV. J. Am. Chem. Soc.: 2006; 128 5620
61. Mans DJ, Cox GA, RajanBabu TV. J. Am. Chem. Soc.: 2011; 133 5776
62. Liang B, Novak T, Tan Z, Negishi E. J. Am. Chem. Soc.: 2006; 128 2770
63. Zhu G, Negishi E. Org. Lett.: 2007; 9 2771
64. Novak T, Tan Z, Liang B, Negishi E. J. Am. Chem. Soc.: 2005; 127 2838
65. Cesati RR III, de Armas J, Hoveyda AH. J. Am. Chem. Soc.: 2004; 126 96
66. Rathgeb X, March S, Alexakis A. J. Org. Chem.: 2006; 71 5737
67. Endo K, Ogawa M, Shibata T. Angew. Chem. Int. Ed.: 2010; 49 2410
68. Luchaco-Cullis CA, Hoveyda AH. J. Am. Chem. Soc.: 2002; 124 8192
69. Wu J, Mampreian DM, Hoveyda AH. J. Am. Chem. Soc.: 2005; 127 4584
70. Alexakis A, Albrow V, Biswas K, d'Augustin M, Prieto O, Woodward S. Chem. Commun.: 2005; 2843
71. Pizzuti MG, Minnaard AJ, Feringa BL. Org. Biomol. Chem.: 2008; 6 3464
72. May TL, Brown MK, Hoveyda AH. Angew. Chem. Int. Ed.: 2008; 47 7358
73. Vuagnoux-d'Augustin M, Alexakis A. Tetrahedron Lett.: 2007; 48 7408
74. Gremaud L, Alexakis A. Angew. Chem. Int. Ed.: 2012; 51 794
75. Lautens M, Renaud J.-L, Hiebert S. J. Am. Chem. Soc.: 2000; 122 1804
76. Lautens M, Hiebert S. J. Am. Chem. Soc.: 2004; 126 1437
77. Priego J, Mancheo OG, Cabrera S, Arrays RG, Llamas T, Carretero JC. Chem. Commun.: 2002; 2512
78. Endo K, Tanaka K, Ogawa M, Shibata T. Org. Lett.: 2011; 13 868
79. Lautens M, Hiebert S, Renaud J.-L. Org. Lett.: 2000; 2 1971
80. Nagib DA, Scott ME, MacMillan DW. C. J. Am. Chem. Soc.: 2009; 131 10875
81. Allen AE, MacMillan DW. C. J. Am. Chem. Soc.: 2010; 132 4986