Preparation of chiral secondary boronic esters via copper-catalyzed enantioselective conjugate reduction of β-boronyl-β-alkyl α,β-unsaturated esters

Tetrahedron

Volumn 68, Issue 17, 2012, Pages 3428-3434

  Ding, Jinyue ^a   Hall, Dennis G ^a  

^a UNIVERSITY OF ALBERTA   (Canada)

Author keywords

Boronoacrylates; Asymmetric reduction; Chiral alkylboronates; Copper (I); Polymethylhydrosiloxane

Indexed keywords

BORONIC ACID DERIVATIVE; COPPER; ETHYL 3 (4,4,5,5 TETRAMETHYL 1,3,2 DIOXABOROLAN 2 YL)BUT 2 ENOATE; ETHYL 3 (4,4,5,5 TETRAMETHYL 1,3,2 DIOXABOROLAN 2 YL)BUTANOATE; ETHYL 3 (4,4,5,5 TETRAMETHYL 1,3,2 DIOXABOROLAN 2 YL)HEXANOATE; ETHYL 3 (4,4,5,5 TETRAMETHYL 1,3,2 DIOXABOROLAN 2 YL)NON 2 ENOATE; ETHYL 3 (4,4,5,5 TETRAMETHYL 1,3,2 DIOXABOROLAN 2 YL)PEN 2 ENOATE; ETHYL 3 (4,4,5,5 TETRAMETHYL 1,3,2 DIOXABOROLAN 2 YL)PENTANOATE; ETHYL 3 CYCLOHEXYL 3 (4,4,5,5 TETRAMETHYL 1,3,2 DIOXABOROLAN 2 YL)ACRYLATE; ETHYL 3 CYCLOHEXYL 3 (4,4,5,5 TETRAMETHYL 1,3,2 DIOXABOROLAN 2 YL)PROPANOATE; ETHYL 3 HEXYL 3 (4,4,5,5 TETRAMETHYL 1,3,2 DIOXABOROLAN 2 YL)PROPANOATE; METHYL 3 (4,4,5,5, TETRAMETHYL 1,3,2 DIOXABOROLAN 2 YL)PENTANOATE; POLYMETHYLHYDROSILOXANE; UNCLASSIFIED DRUG;

CATALYST; CONFERENCE PAPER; ENANTIOMER; ENANTIOSELECTIVITY; PRIORITY JOURNAL; REDUCTION;

EID: 84859547593     PISSN: 00404020     EISSN: 14645416     Source Type: Journal    
DOI: 10.1016/j.tet.2011.07.088     Document Type: Conference Paper

References (45)

1. D.G. Hall Boronic Acids 2005 Wiley-VCH Weinheim
2. D.S. Matteson Tetrahedron 54 1998 10555 10607
3. X. Gao, and D.G. Hall J. Am. Chem. Soc. 125 2003 9308 9309
4. C.M. Crudden, Y.B. Hleba, and A.C. Chen J. Am. Chem. Soc. 126 2004 9200 9201
5. X. Gao, and D.G. Hall J. Am. Chem. Soc. 127 2005 1628 1629
6. X. Gao, D.G. Hall, M. Deligny, A. Favre, F. Carreaux, and B. Carboni Chem. - Eur. J. 13 2006 3132 3142
7. L. Carosi, and D.G. Hall Can. J. Chem. 87 2009 650 661
8. S. Lessard, F. Peng, and D.G. Hall J. Am. Chem. Soc. 131 2009 9612 9613
9. S.P. Thomas, R.M. French, V. Jheengut, and V.K. Aggarwal Chem. Rec. 9 2009 24 39
10. A. Ros, and V.K. Aggarwal Angew. Chem., Int. Ed. 48 2009 6289 6292
11. G. Dutheuil, M.P. Webster, P.A. Worthington, and V.K. Aggarwal Angew. Chem., Int. Ed. 48 2009 6317 6319
12. S.P. Thomas, and V.K. Aggarwal Angew. Chem., Int. Ed. 48 2009 1896 1898
13. F. Schmidt, F. Keller, E. Vedrenne, and V.K. Aggarwal Angew. Chem., Int. Ed. 48 2009 1149 1152
14. D. Noh, H. Chea, J. Ju, and J. Yun Angew. Chem., Int. Ed. 48 2009 6062 6064
15. K.-S. Lee, A.R. Zhugralin, and A.H. Hoveyda J. Am. Chem. Soc. 131 2009 7253 7255
16. R.J. Ely, and J.P. Morken Org. Lett. 12 2010 4348 4351
17. D. Imao, B.W. Glasspoole, V.S. Laberge, and C.M. Crudden J. Am. Chem. Soc. 131 2009 5024 5025
18. C.M. Crudden, B.W. Glasspoole, and C.J. Lata Chem. Commun. 2009 6704 6716
19. T. Ohmura, T. Awano, and M. Suginome J. Am. Chem. Soc. 132 2010 13191 13193
20. D. Sandrock, L. Jean-Gérard, C.Y. Chen, S.D. Dreher, and G.A. Molander J. Am. Chem. Soc. 132 2010 17109 17110
21. I.C. Stewart, R.G. Bergman, and F.D. Toste J. Am. Chem. Soc. 125 2003 8696 9697
22. D.B. Ramachary, and R. Mondal Tetrahedron Lett. 47 2006 7689 7693
23. J.A. Schiffner, K. Müther, and M. Oestreich Angew. Chem., Int. Ed. 49 2010 1194 1196
24. S. Mun, J.-E. Lee, and J. Yun Org. Lett. 8 2006 4887 4889
25. J.-E. Lee, and J. Yun Angew. Chem., Int. Ed. 47 2008 145 147
26. H.-S. Sim, X. Feng, and J. Yun Chem. - Eur. J. 15 2009 1939 1943
27. H. Chea, H. Sim, and J. Yun Adv. Synth. Catal. 351 2009 855 858
28. V. Lillo, A. Prieto, A. Bonet, M.M. Díaz-Requejo, J. Ramírez, P.J. Pérez, and E. Fernández Organometallics 28 2009 659 662
29. W.J. Fleming, H. Müller-Bunz, V. Lillo, E. Fernández, and P.J. Guiry Org. Biomol. Chem. 7 2009 2520 2524
30. V. Lillo, M.J. Geier, S.A. Westcott, and E. Fernández Org. Biomol. Chem. 7 2009 4674 4676
31. Y. Lee, and A.H. Hoveyda J. Am. Chem. Soc. 131 2009 3160 3161
32. I.-H. Chen, L. Yin, W. Itano, M. Kanai, and M. Shibasaki J. Am. Chem. Soc. 131 2009 11664 11665
33. T. Shiomi, T. Adachi, K. Toribatake, L. Zhou, and H. Nishiyama Chem. Commun. 2009 5987 5989
34. J.C.H. Lee, and D.G. Hall J. Am. Chem. Soc. 132 2010 5544 5545
35. B.H. Lipshutz, J.M. Servesko, and B.R. Taft J. Am. Chem. Soc. 126 2004 8352 8353
36. B.H. Lipshutz, J.M. Servesko, T.B. Petersen, P.P. Papa, and A.A. Lover Org. Lett. 6 2004 1273 1275
37. J.-E. Lee, J. Kwon, and J. Yun Chem. Commun. 2008 733 734
38. T. Ishiyama, J. Takagi, A. Kamon, and N. Miyaura J. Organomet. Chem. 687 2003 284 290
39. For the preparation of the vinyl triflates, see: D. Babonski, O. SOltani, and D.E. Frantz Org. Lett. 13 2008 2901 2904
40. D.H. Appella, Y. Moritani, R. Shintani, E.M. Ferreira, and S.L. Buchwald J. Am. Chem. Soc. 121 1999 9473 9474
41. W.S. Mahoney, D.M. Brestensky, and J.M. Stryker J. Am. Chem. Soc. 110 1988 291 293
42. For the application of Stryker's reagent, see: S. Rendler, and M. Oestreich Angew. Chem., Int. Ed. 46 2007 498 504
43. C. Deutsch, N. Krause, and B.H. Lipshutz Chem. Rev. 108 2008 2916 2927
44. D. Lee, D. Kim, and J. Yun Angew. Chem., Int. Ed. 45 2006 2785 2787
45. D. Lee, Y. Yang, and J. Yun Org. Lett. 9 2007 2749 2751