Protecting-group-free diastereoselective C-C coupling of 1,3-glycols and allyl acetate through site-selective primary alcohol dehydrogenation

Angewandte Chemie - International Edition

Volumn 52, Issue 11, 2013, Pages 3195-3198

  Dechert Schmitt, Anne Marie R ^a   Schmitt, Daniel C ^a   Krische, Michael J ^a  

^a UNIVERSITY OF TEXAS AT AUSTIN   (United States)

Author keywords

allylation; diastereoselectivity; iridium; polyketides; transfer hydrogenation

Indexed keywords

CHIRAL AUXILIARIES; DIASTEREO-SELECTIVITY; DIASTEREOSELECTIVE; POLYKETIDES; PRIMARY ALCOHOLS; PROTECTING GROUP; SITE SELECTIVE; TRANSFER HYDROGENATIONS;

ALLYLATION; DEHYDROGENATION; EXCITONS; IRIDIUM; VOLATILE FATTY ACIDS;

STEREOSELECTIVITY;

ACETIC ACID DERIVATIVE; ALCOHOL DERIVATIVE; ALLYL ACETATE; ALLYL COMPOUND; GLYCOL; IRIDIUM; ORGANOMETALLIC COMPOUND; POLYKETIDE;

ARTICLE; CHEMISTRY; STEREOISOMERISM;

ACETATES; ALCOHOLS; ALLYL COMPOUNDS; GLYCOLS; IRIDIUM; ORGANOMETALLIC COMPOUNDS; POLYKETIDES; STEREOISOMERISM;

EID: 84874926399     PISSN: 14337851     EISSN: 15213773     Source Type: Journal    
DOI: 10.1002/anie.201209863     Document Type: Article

References (72)

1. The term chemoselectivity broadly refers to the ability to selectively act upon like or unlike functional groups:, B. M. Trost, Science 1983, 219, 245-250. The term site-selectivity will be used in the more specific context of discrimination between like functional groups en route to constitutionally isomeric products.
2. I. S. Young, P. S. Baran, Nat. Chem. 2009, 1, 193-205.
3. K. S. Griswold, S. J. Miller, Tetrahedron 2003, 59, 8869-8875
4. C. A. Lewis, B. R. Sculimbrene, Y. Xu, S. J. Miller, Org. Lett. 2005, 7, 3021-3023
5. C. A. Lewis, S. J. Miller, Angew. Chem. 2006, 118, 5744-5747
6. Angew. Chem. Int. Ed. 2006, 45, 5616-5619
7. C. A. Lewis, J. Merkel, S. J. Miller, Bioorg. Med. Chem. Lett. 2008, 18, 6007-6011
8. C. A. Lewis, K. E. Longcore, S. J. Miller, P. A. Wender, J. Nat. Prod. 2009, 72, 1864-1869
9. B. S. Fowler, K. M. Laemmerhold, S. J. Miller, J. Am. Chem. Soc. 2012, 134, 9755-9761.
10. D. Lee, M. S. Taylor, J. Am. Chem. Soc. 2011, 133, 3724-3727
11. L. Chan, M. S. Taylor, Org. Lett. 2011, 13, 3090-3093
12. C. Gouliaras, D. Lee, L. Chan, M. S. Taylor, J. Am. Chem. Soc. 2011, 133, 13926-13929
13. D. Lee, C. L. Williamson, L. Chan, M. S. Taylor, J. Am. Chem. Soc. 2012, 134, 8260-8267.
14. I. J. S. Fairlamb, Chem. Soc. Rev. 2007, 36, 1036-1045
15. L. Joucla, L. Djakovitch, Adv. Synth. Catal. 2009, 351, 673-714
16. J.-R. Wang, K. Manabe, Synthesis 2009, 1405-1427
17. R. Rossi, F. Bellina, M. Lessi, Adv. Synth. Catal. 2012, 354, 1181-1255.
18. F. Kakiuchi, S. Murai, Top. Organomet. Chem. 1999, 3, 47-79
19. D. H. R. Barton, Tetrahedron 1998, 54, 5805-5817
20. H. M. L. Davies, D. Morton, Chem. Soc. Rev. 2011, 40, 1857-1869
21. S. R. Neufeldt, M. S. Sanford, Acc. Chem. Res. 2012, 45, 936-946
22. K. M. Engle, T.-S. Mei, M. Wasa, J.-Q. Yu, Acc. Chem. Res. 2012, 45, 788-802
23. O. Daugulis, Top. Curr. Chem. 2010, 292, 57-84
24. T. Newhouse, P. S. Baran, Angew. Chem. 2011, 123, 3422-3435
25. Angew. Chem. Int. Ed. 2011, 50, 3362-3374.
26. Y. Lin, X. Zhu, Y. J. Zhou, Organomet. Chem. 1992, 429, 269-274
27. T. Suzuki, K. Morita, M. Tsuchida, K. Hiroi, Org. Lett. 2002, 4, 2361-2363
28. T. Suzuki, T. Yamada, K. Watanabe, T. Katoh, Bioorg. Med. Chem. Lett. 2005, 15, 2583-2585
29. T. Suzuki, K. Morita, H. Ikemiyagi, K. Watanabe, K. Hiroi, T. Katoh, Heterocycles 2006, 69, 457-461
30. M. Königsmann, N. Donati, D. Stein, H. Schönberg, J. Harmer, A. Sreekanth, H. Grützmacher, Angew. Chem. 2007, 119, 3637-3640
31. Angew. Chem. Int. Ed. 2007, 46, 3567-3570
32. C. Oger, Y. Brinkmann, S. Bouazzaoui, T. Durand, J.-M. Galano, Org. Lett. 2008, 10, 5087-5090
33. S. Arita, T. Koike, Y. Kayaki, T. Ikariya, Chem. Asian J. 2008, 3, 1479-1485
34. M. Kosaka, S. Sekiguchi, J. Naito, M. Uemura, S. Kuwahara, M. Watanabe, N. Harada, K. Hiroi, Chirality 2005, 17, 218-232
35. T. Suzuki, K. Morita, Y. Matsuo, K. Hiroi, Tetrahedron Lett. 2003, 44, 2003-2006.
36. For an excellent review on iridium-catalyzed oxidation, see:, T. Suzuki, Chem. Rev. 2011, 111, 1825-1845.
37. N. Z. Burns, P. S. Baran, R. W. Hoffmann, Angew. Chem. 2009, 121, 2896-2910
38. Angew. Chem. Int. Ed. 2009, 48, 2854-2867.
39. J. F. Bower, I. S. Kim, R. L. Patman, M. J. Krische, Angew. Chem. 2009, 121, 36-48
40. Angew. Chem. Int. Ed. 2009, 48, 34-46
41. R. L. Patman, J. F. Bower, I. S. Kim, M. J. Krische, Aldrichimica Acta 2008, 41, 95-104
42. S. B. Han, I. S. Kim, M. J. Krische, Chem. Commun. 2009, 7278-7287
43. J. F. Bower, M. J. Krische, Top. Organomet. Chem. 2011, 34, 107-138
44. A. Hassan, M. J. Krische, Org. Process Res. Dev. 2011, 15, 1236-1242
45. J. Moran, M. J. Krische, Pure Appl. Chem. 2012, 84, 1729-1739.
46. I. S. Kim, M.-Y. Ngai, M. J. Krische, J. Am. Chem. Soc. 2008, 130, 6340-6341
47. I. S. Kim, M.-Y. Ngai, M. J. Krische, J. Am. Chem. Soc. 2008, 130, 14891-14899
48. I. S. Kim, S. B. Han, M. J. Krische, J. Am. Chem. Soc. 2009, 131, 2514-2520
49. Y. Lu, M. J. Krische, Org. Lett. 2009, 11, 3108-3111
50. A. Hassan, Y. Lu, M. J. Krische, Org. Lett. 2009, 11, 3112-3115
51. X. Gao, I. A. Townsend, M. J. Krische, J. Org. Chem. 2011, 76, 2350-2354
52. D. C. Schmitt, A.-M. R. Dechert-Schmitt, M. J. Krische, Org. Lett. 2012, 14, 6302-6305.
53. P. V. Ramachandran, Aldrichimica Acta 2002, 35, 23-35
54. S. E. Denmark, J. Fu, Chem. Rev. 2003, 103, 2763-2794
55. C.-M. Yu, J. Youn, H.-K. Jung, Bull. Korean Chem. Soc. 2006, 27, 463-472
56. I. Marek, G. Sklute, Chem. Commun. 2007, 1683-1691
57. D. G. Hall, Synlett 2007, 1644-1655
58. H. Lachance, D. G. Hall, Org. React. 2008, 73, 1-544
59. M. Yus, J. C. Gonzalez-Gomez, F. Foubelo, Chem. Rev. 2011, 111, 7774-7854.
60. N. Minami, S. S. Ko, Y. Kishi, J. Am. Chem. Soc. 1982, 104, 1109-1111
61. S. Y. Ko, A. W. M. Lee, S. Masamune, L. A. Reed, K. B. Sharpless III, F. J. Walker, Science 1983, 220, 949-951
62. S. Kobayashi, A. Ohtsubo, T. Mukaiyama, Chem. Lett. 1991, 831-834
63. A. Hammadi, J. M. Nuzillard, J. C. Poulin, H. B. Kagan, Tetrahedron: Asymmetry 1992, 3, 1247-1262
64. M. P. Doyle, A. V. Kalinin, D. G. Ene, J. Am. Chem. Soc. 1996, 118, 8837-8846
65. B. M. Trost, T. L. Calkins, C. Oertelt, J. Zambrano, Tetrahedron Lett. 1998, 39, 1713-1716
66. E. P. Balskus, E. N. Jacobsen, Science 2007, 317, 1736-1740
67. S. B. Han, J. R. Kong, M. J. Krische, Org. Lett. 2008, 10, 4133-4135.
68. F. Fu, T.-P. Loh, Tetrahedron Lett. 2009, 50, 3530-3533.
69. A. Mengel, O. Reiser, Chem. Rev. 1999, 99, 1191-1223.
70. L. A. Paquette, T. M. Mitzel, J. Am. Chem. Soc. 1996, 118, 1931-1937
71. S. BouzBouz, J. Cossy, Org. Lett. 2000, 2, 501-504.
72. "The ideal synthesis creates a complex skeleton. in a sequence only of successive construction reactions involving no intermediary refunctionalizations, and leading directly to the structure of the target, not only its skeleton but also its correctly placed functionality.", J. B. Hendrickson, J. Am. Chem. Soc. 1975, 97, 5784-5800.