Pinene-derived iminodiacetic acid (PIDA): A powerful ligand for stereoselective synthesis and iterative cross-coupling of C(sp 3) boronate building blocks

Journal of the American Chemical Society

Volumn 133, Issue 35, 2011, Pages 13774-13777

  Li, Junqi ^a   Burke, Martin D ^a  

^a UNIVERSITY OF ILLINOIS AT URBANA CHAMPAIGN   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

BIFUNCTIONAL REAGENTS; BORONATE; BUILDING BLOCKES; CROSS-COUPLINGS; DIASTEREOSELECTIVE SYNTHESIS; IMINODIACETIC ACID; SMALL MOLECULES; STEREOCHEMICAL PURITY; STEREOSELECTIVE SYNTHESIS;

ALDEHYDES; LIGANDS; OLEFINS; STEREOCHEMISTRY; STEREOSELECTIVITY; SYNTHESIS (CHEMICAL);

CHELATION;

ALDEHYDE DERIVATIVE; ALKENE; BORONIC ACID DERIVATIVE; DIGLYCINE; PINENE;

ARTICLE; CHIRALITY; CROSS COUPLING REACTION; ENANTIOSELECTIVITY; HYBRIDIZATION; PROTON NUCLEAR MAGNETIC RESONANCE; STEREOCHEMISTRY; SYNTHESIS; X RAY CRYSTALLOGRAPHY;

BORONIC ACIDS; IMINO ACIDS; LIGANDS; MONOTERPENES; STEREOISOMERISM;

EID: 80052305738     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja205912y     Document Type: Article

References (66)

1. Gillis, E. P.; Burke, M. D. J. Am. Chem. Soc. 2007, 129, 6716-6717
2. Gillis, E. P.; Burke, M. D. Aldrichimica Acta 2009, 42, 17-27
3. Gillis, E. P.; Burke, M. D. J. Am. Chem. Soc. 2008, 130, 14084-14085
4. Lee, S. J.; Gray, K. C.; Paek, J. S.; Burke, M. D. J. Am. Chem. Soc. 2008, 130, 466-468
5. Knapp, D. M.; Gillis, E. P.; Burke, M. D. J. Am. Chem. Soc. 2009, 131, 6961-6963
6. Uno, B. E.; Gillis, E. P.; Burke, M. D. Tetrahedron 2009, 65, 3130-3138
7. Woerly, E. M.; Cherney, A. H.; Davis, E. K.; Burke, M. D. J. Am. Chem. Soc. 2010, 132, 6941-6943
8. Lee, S. J.; Anderson, T. M.; Burke, M. D. Angew. Chem., Int. Ed. 2010, 49, 8860-8863
9. Struble, J. R.; Lee, S. J.; Burke, M. D. Tetrahedron 2010, 66, 4710-4718
10. Dick, G. D.; Knapp, D. M.; Gillis, E. P.; Burke, M. D. Org. Lett. 2010, 12, 2314-2317
11. Woerly, E. M.; Struble, J. R.; Palyam, N.; OHara, S. P.; Burke, M. D. Tetrahedron 2011, 67, 4333-4343
12. Fujii, S.; Chang, S. Y.; Burke, M. D. Angew. Chem., Int. Ed. [Online early access]. DOI: 10.1002/anie.201102688. Published Online: June 16, 2011.
13. More than 75 MIDA boronates are now commercially available.
14. Brak, K.; Ellman, J. A. J. Org. Chem. 2010, 75, 3147-3150
15. Brak, K.; Ellman, J. A. Org. Lett. 2010, 12, 2004-2007
16. Brenzovich, W. E.; Brazeau, J.-F.; Toste, F. D. Org. Lett. 2010, 12, 4728-4731
17. Burns, A. R.; McAllister, G. D.; Shanahan, S. E.; Taylor, R. J. K. Angew. Chem., Int. Ed. 2010, 49, 5574-5577
18. Han, J.; Xu, B.; Hammond, G. B. J. Am. Chem. Soc. 2010, 132, 916-917
19. Gustafson, J. L.; Lim, D.; Barrett, K. T.; Miller, S. J. Angew. Chem., Int. Ed. 2011, 50, 5125-5129
20. Chan, M. W. J.; Amarante, G. W.; Toste, F. D. Tetrahedron 2011, 67, 4306-4312
21. Grob, J. E.; Nunez, J.; Dechantsreiter, M. A.; Hamann, L. G. J. Org. Chem. 2011, 76, 4930-4940
22. Colgin, N.; Finn, T.; Cobb, S. L. Org. Biomol. Chem. 2011, 9, 1864-1870
23. Mohamed, Y. M. A.; Hansen, T. V. Tetrahedron Lett. 2011, 52, 1057-1059
24. Imao, D.; Glasspole, B. W.; Laberge, V. S.; Crudden, C. M. J. Am. Chem. Soc. 2009, 131, 5024-5025
25. Crudden, C. M. Abstr. Pap.-Am. Chem. Soc. 2011, 241, ORGN 323
26. Owston, N. A.; Fu, G. C. J. Am. Chem. Soc. 2010, 132, 11908-11909
27. Lundin, P. M.; Fu, G. C. J. Am. Chem. Soc. 2010, 132, 11027-11029
28. Saito, B.; Fu, G. C. J. Am. Chem. Soc. 2008, 130, 6694-6695
29. Ohmura, T.; Awano, T.; Suginome, M. J. Am. Chem. Soc. 2010, 132, 13191-13193
30. Sandrock, D. L.; Jean-Gerard, L.; Chen, C.-Y.; Dreher, S. D.; Molander, G. A. J. Am. Chem. Soc. 2010, 132, 17108-17110
31. Dreher, S. D.; Dormer, P. G.; Sandrock, D. L.; Molander, G. A. J. Am. Chem. Soc. 2008, 130, 9257-9259
32. Crudden, C. M.; Glasspoole, B. W.; Lata, C. J. Chem. Commun. 2009, 6704-6716
33. Hall, D. G. Boronic Acids; Wiley-VCH: Weinheim, Germany, 2005.
34. Matteson, D. S. Tetrahedron 1998, 54, 10555-10607
35. Crudden, C. M.; Hleba, Y. B.; Chen, A. C. J. Am. Chem. Soc. 2004, 126, 9200-9201
36. Pelz, N. F.; Woodward, A. R.; Burks, H. E.; Sieber, J. D.; Morken, J. P. J. Am. Chem. Soc. 2004, 126, 16328-16329
37. Kliman, L. T.; Mlynarski, S. N.; Morken, J. P. J. Am. Chem. Soc. 2009, 131, 13210-13211
38. OBrien, J. M.; Lee, K.; Hoveyda, A. H. J. Am. Chem. Soc. 2010, 132, 10630-10633
39. Chen, I.-H.; Yin, L.; Itano, W.; Kanai, M.; Shibasaki, M. J. Am. Chem. Soc. 2009, 131, 11664-11665
40. Lee, J. C. H.; Hall, D. G. J. Am. Chem. Soc. 2010, 132, 5544-5545
41. Bagutski, V.; French, R. M.; Aggarwal, V. K. Angew. Chem., Int. Ed. 2010, 49, 5142-5145
42. Thomas, S. P.; French, R. M.; Jheengut, V.; Aggarwal, V. K. Chem. Rec. 2009, 9, 24-39
43. Noh, D.; Chea, H.; Ju, J.; Yun, J. Angew. Chem., Int. Ed. 2009, 48, 6062-6064
44. Gonzalez, A. Z.; Román, J. G.; Gonzalez, E.; Martinez, J.; Medina, J. R.; Matos, K.; Soderquist, J. A. J. Am. Chem. Soc. 2008, 130, 9218-9219
45. Mancilla, T.; Contreras, R.; Wrackmeyer, B. J. Organomet. Chem. 1986, 307, 1-6
46. Mancilla, T.; Zamudio-Rivera, L. S.; Beltrán, H. I.; Santillan, R.; Farfán, N. ARKIVOC 2005, vi) 366-376
47. Fernandez, E.; Frey, W.; Pietruszka, J. Synlett 2009, 9, 1386-1388
48. Luithle, J. E. A.; Pietruszka, J. J. Org. Chem. 1999, 64, 8287-8297
49. Pietruszka, J.; Schöne, N. Angew. Chem., Int. Ed. 2003, 42, 5638-5641
50. Hussain, M. H.; Toribio, J. H.; Carroll, P. J.; Walsh, P. J. Angew. Chem., Int. Ed. 2011, 50, 6337-6340
51. Molander, G. A.; Ribagorda, M. J. Am. Chem. Soc. 2003, 125, 11148-11149
52. For the non-stereoselective epoxidation of MIDA boronates, see ref 2d.
53. Brown, H. C.; Jadhav, P. K. J. Am. Chem. Soc. 1983, 105, 2092-2093
54. Rathke, M. W.; Millard, A. A. Organic Syntheses; Wiley: New York, 1988; Collect. Vol. VI, p 943.
55. Thomas, S. P.; Aggarwal, V. K. Angew. Chem., Int. Ed. 2009, 48, 1896-1898
56. Meinwald, J.; Labana, S. S.; Chadha, M. S. J. Am. Chem. Soc. 1963, 85, 582-585
57. Eisch, J. J.; Trainor, J. T. J. Org. Chem. 1963, 28, 2870-2876
58. Yudin, A. K. Private communication.
59. He, Z.; Yudin, A. K. J. Am. Chem. Soc., in press; DOI: 10.1021/ja205910d.
60. Hili, R.; Rai, V.; Yudin, A. K. J. Am. Chem. Soc. 2010, 132, 2889-2891
61. Hili, R.; Yudin, A. K. J. Am. Chem. Soc. 2009, 131, 16404-16406
62. Li, X.; Yudin, A. K. J. Am. Chem. Soc. 2007, 129, 14152-14153
63. Hili, R.; Yudin, A. K. J. Am. Chem. Soc. 2006, 128, 14772-14773
64. Baktharaman, S.; Hili, R.; Yudin, A. K. Aldrichimica Acta 2008, 41, 109-118
65. Afagh, N. A.; Yudin, A. K. Angew. Chem., Int. Ed. 2010, 49, 262-310
66. Stelmach, J. E.; Keith, R.; Parmee, E. R.; Tata, J. R. PCT/US2006/009694, Sep 28, 2006.