An N-linked bidentate phosphoramidite ligand (N-Me-BIPAM) for rhodium-catalyzed asymmetric 1,4-Addition of arylboronic acids to α,β-unsaturated ketones

Molecules

Volumn 18, Issue 1, 2013, Pages 14-26

  Yamamoto, Yasunori ^a   Kurihara, Kazunori ^a   Takahashi, Yoshinori ^a   Miyaura, Norio ^a  

^a HOKKAIDO UNIVERSITY   (Japan)

Author keywords

Asymmetric conjugate addition; Bidentate phosphoramidite ligand; Rhodium catalyst

Indexed keywords

BORONIC ACID DERIVATIVE; KETONE; LIGAND; ORGANOPHOSPHORUS COMPOUND; PHOSPHORAMIDOUS ACID; RHODIUM;

ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; CHEMISTRY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; SYNTHESIS;

BORONIC ACIDS; CATALYSIS; KETONES; LIGANDS; MAGNETIC RESONANCE SPECTROSCOPY; MOLECULAR STRUCTURE; ORGANOPHOSPHORUS COMPOUNDS; RHODIUM;

MLCS; MLOWN;

EID: 84872858641     PISSN: None     EISSN: 14203049     Source Type: Journal    
DOI: 10.3390/molecules18010014     Document Type: Article

References (59)

1. Krause, N.; Hoffmann-Röder, A. Recent advances in catalytic enantioselective Michael additions. Synthesis 2001, 2001, 171-196.
2. Tomioka, K.; Nagaoka, Y. Conjugate Addition of Organometallic Reagents. In Comprehensive Asymmetric Catalysis; Jacobsen, E.N., Pfalts, A., Yamamoto, H., Eds.; Springer Verlag: Berlin, Germany, 1999; Chapter 31.1, pp. 1105-1120.
3. Chan, A.S.C.; Kwong, F.Y.; Lu, G. C-C Bond Formation through Conjugate Addition of C-M to C=C-C=O and C=C-NO2. In Comprehensive Organometallic Chemistry III; Crabtree, R.H., Mingos, S.M.P., Eds.; Elsevier: Oxford, UK, 2007; Volume 10, Chapter 10.08, pp. 369-491.
4. Hayashi, T. Rhodium-catalyzed asymmetric 1,4-Addition of organoboronic acids and their derivatives to electron deficient olefins. Synlett 2001, 2001, 879-887.
5. Fagnou, K.; Lautens, M. Rhodium-catalyzed carbon-carbon bond forming reactions of organometallic compounds. Chem. Rev. 2003, 103, 169-196.
6. Hayashi, T.; Yamazaki, K. Rhodium-catalyzed asymmetric 1,4-Addition and its related asymmetric reactions. Chem. Rev. 2003, 103, 2829-2844.
7. Tian, P.; Dong, H.-Q.; Lin, G.-Q. Rhodium-catalyzed asymmetric arylation. ACS Catal. 2012, 2, 95-119.
8. Berthon-Gelloz, G.; Hayashi, T. Rhodium-catalyzed asymmetric conjugate addition of organoboronic acids. In Boronic Acids Preparation and Applications in Organic Synthesis, Medicine and Materials, 2nd ed.; Hall, D.G., Ed.; Wiley-VHC: Weinheim, Germany, 2011; Chapter 5, pp. 263-313.
9. Narui, R.; Hayashi, S.; Oromo, H.; Shintani, R.; Hayashi, T. (S)-Phenylalanine-derived chiral phosphorus-olefin ligands in rhodium-catalyzed asymmetric 1,4-Addition reactions. Tetrahedron Asymmetry 2012, 23, 284-293.
10. Grugel, H.; Albrecht, F.; Minuth, T.; Boysen, M.M. Efficient pseudo-enantiomeric carbohydrate olefin ligands. Org. Lett. 2012, 14, 3780-3783.
11. Jin, S.-S.; Wang, H.; Zhu, T.-S.; Xu, M.-H. Design of N-cinnamyl sulfinamides as new sulfur-containing olefin ligands for asymmetric catalysis: Achieving structural simplicity with a categorical linear framework. Org. Biomol. Chem. 2012, 10, 1764-1768.
12. Xue, F.; Li, X.; Wan, B. A class of benzene backbone-base olefin-sulfoxide ligands for Rh-catalyzed enantioselective addition of arylboronic acids to enones. J. Org. Chm. 2011, 76, 7256-7262.
13. Qi, W.-Y.; Zhu, T.-S.; Xu, M.-H. Design of chiral sulfoxide-olefins as a new class of sulfur-based olefin ligands for asymmetric catalysis. Org. Lett. 2011, 13, 3410-3413.
14. Jin, S.-S.; Wang, H.; Xu, M.-H. Design of N-sulfinyl homoallylic amines as novel sulfinamideolefin hybrid ligands for asymmetric catalysis: Application in Rh-catalyzed enantioselective 1,4-Additions. Chem. Commun. 2011, 47, 7230-7232.
15. Thaler, T.; Guo, L.-N.; Steibo, A.K.; Raducan, M.; Karaghiosoff, K.; Mayer, P.; Knochel, P. Sulfoxide-Alkene hybrids: A new class of chiral ligands for the Hayashi-Miyaura reaction. Org. Lett. 2011, 13, 3182-3185.
16. Feng, X.; Wei, B.; Yang, J.; Du, H. Chiral N-tert-butanesulfinyl a,b-unsaturated ketimine: A simple and highly effective olefin/sulfinimide hybrid ligand for asymmetric 1,4-Additions. Org. Biomol. Chem. 2011, 9, 5927-5929.
17. Chen, G.; Gui, J.; Li, L.; Liao, J. Chiral sulfoxide-olefin ligands: Completely switchable stereoselective in rhodium-catalyzed asymmetric conjugate additions. Angew. Chem. Int. Ed. Engl. 2011, 50, 7681-7685.
18. Hahn, B.T.; Tewes, F.; Fröhlich, R.; Glorius, F. Olefin-oxazolines (OlefOx): Highly modular, easoly tunable ligands for asymmetric catalysis. Angew. Chem. Int. Ed. Engl. 2010, 49, 1143-1146.
19. Lang, F.; Li, D.; Chen, J.; Chen, J.; Li, L.; Cun, L.; Zhu, J.; Deng, J.; Liao, J. tert-Butanesulfinylphosphines: Simple chiral ligands in rhodium-catalyzed asymmetric addition of arylboronic acids to electron-deficient olefins. Adv. Synth. Catal. 2010, 352, 843-846.
20. Bürgi, J.J.; Mariz, R.; Gatti, M.; Drinkel, E.; Luan, X.; Blumentritt, S.; Linden, A.; Dorta, R. Unprecedented selectivity via electronic substrate recognition in the 1,4-Addition to cyclic olefins using a chiral disulfoxide rhodium catalyst. Angew. Chem. Int. Ed. Engl. 2009, 48, 2768-2771.
21. Mariz, R.; Luan, X.; Gatti, M.; Linden, A.; Dorta, R. A chiral bis-sulfoxide ligand in late-transition metal catalysis; rhodium-catalyzed asymmetric addition of arylboronic acids to electron-deficient olefins. J. Am. Chem. Soc. 2008, 130, 2172-2173.
22. Iguchi, Y.; Itooka, R.; Miyaura, N. Asymmetric conjugate addition of arylboronic acids to enones catalyzed by rhodium-monodentate phosphoramidite Complexes in the presence of vases. Synlett 2003, 2003, 1040-1042.
23. Boiteau, J.-G.; Imbos, R.; Minnerd, A.J.; Feringa, B.L. Rhodium-catalyzed asymmetric conjugate additions of boronic acids using monodentate phosphoramidite ligands. Org. Lett. 2003, 5, 681-684.
24. Duursma, A.; Hen, J.; Schuppan, J.; Minnerd, J.; Feringa, B.L. First examples of improved catalytic asymmetric C-C bond formation using the monodentate ligand combination approach. Org. Lett. 2003, 5, 3111-3113.
25. Boiteau, J.-G.; Minnerd, A.J.; Feringa, B.L. High efficiency and enantioselectivity in the Rh-catalyzed conjugate addition of arylboronic acids using monodentate phosphoramidites. J. Org. Chem. 2003, 68, 9481-9484.
26. Duursma, A.; Boiteau, J.-G.; Lefort, L.; Boorgers, J.A.F.; de Vries, A.H.M.; de Vries, J.G.; Minnerd, A.J.; Feringa, B.L. Highly enantioselective conjugate additions of potassium organotrifluoroborates to enones by use of monodentate phosphoramidite ligands. J. Org. Chem. 2004, 69, 8045-8052.
27. Martina, S.L.X.; Minnerd, A.J.; Hesssen, B.; Feringa, B.L. Highly enantioselective rhodium-catalyzed conjugate addition of arylboronic acids to enones at room temperature. Tetrahedron Lett. 2005, 46, 7159-7163.
28. Drinkel, E.; Brieño, A.; Dorta, R.; Dorta, R. Hemilabile P-Alkene ligands in chiral rhodium and copper complexes: Catalytic asymmetric 1,4-Additions to enones 2. Organometallics 2010, 29, 2503-2514.
29. Reetz, M.T.; Moulin, D.; Gosberg, A. BINOL-based diphosphonites as ligands in the asymmetric Rh-catalyzed conjugate addition of arylboronic acids. Org. Lett. 2001, 3, 4083-4085.
30. Kuriyama, M.; Tomioka, K. Chiral amidomonophosphine-rhodium(I) catalyst for asymmetric 1,4-Addition of arylboronic acids to cycloalkenones. Tetrahedron Lett. 2001, 42, 921-923.
31. Kuriyama, M.; Nagai, K.; Yamada, K.; Miwa, Y.; Tomioka, K. Hemilabile amidomonophosphine ligand-rhodium(I) complex-catalyzed asymmetric 1,4-Addition of arylboronic acids to cycloalkenones. J. Am. Chem. Soc. 2002, 124, 8932-8939.
32. Ma, Y.; Song, C.; Ma, C.; Sun, Z.; Chai, Q.; Andrus, M.B. asymmetric addition of aryl boron reagents to enones with Rhodium dicyclophane imidazolium carbene catalysis. Angew. Chem. Int. Ed. Engl. 2003, 42, 5871-5874.
33. Becht, J.-M.; Bappert, E.; Helmchen, G. Application of rhodium complexes of chiral diphenylphosphino-functionalized N-heterocyclic carbenes as catalysts in enantioselective conjugate additions of arylboronic acids. Adv. Synth. Catal. 2005, 347, 1495-1498.
34. Imamoto, T.; Sugita, K.; Yoshida, K. An Air-Stable P-Chiral Phosphine Ligand for Highly enantioselective transition-metal-catalyzed reactions. J. Am. Chem. Soc. 2005, 127, 11934-11935.
35. Hayashi, T.; Ueyama, K.; Tokunaga, N.; Yoshida, K. A chiral chelating diene as a new type of chiral ligand for transition metal catalysts: Its preparation and use for the rhodium-catalyzed asymmetric 1,4-Addition. J. Am. Chem. Soc. 2003, 125, 11508-11509.
36. Tokunaga, N.; Otomaru, Y.; Okamoto, K.; Ueyama, K.; Shintani, R.; Hayashi, T. C2-symmetric bicyclo[2.2.2]octadienes as chiral ligands: Their high performance in rhodium-catalyzed asymmetric arylation of N-tosylarylimines. J. Am. Chem. Soc. 2004, 126, 13584-13585.
37. Defieber, C.; Paquin, J.-F.; Serna, S.; Carreira, E.M. Chiral [2.2.2] dienes as ligands for Rh(I) in conjugate additions of boronic acids to a wide range of acceptors. Org. Lett. 2004, 6, 3873-3876.
38. Otomura, Y.; Okamoto, K.; Shintani, R.; Hayashi, T. Preparation of C2-symmetric bicyclo [2.2.2]octa-2,5-diene ligands and their use for rhodium-catalyzed asymmetric 1,4-Addition of arylboronic acids. J. Org. Chem. 2005, 70, 2503-2508.
39. Chen, F.-X.; Kina, A.; Hayashi, T. High performance of a chiral diene-rhodium catalyst for the asymmetric 1,4-Addition of arylboroxines to a,ß-unsaturated ketones. Org. Lett. 2006, 8, 341-344.
40. Feng, C.-G.; Wang, Z.-Q.; Shao, C.; Xu, M.-H.; Lin, G.-Q. Highly practical catalytic asymmetric 1,4-Addition of arylboronic acids in water using new hydrophilic chiral bicyclo[3.3.0]diene ligands. Org. Lett. 2008, 10, 4101-4104.
41. Hu, X.; Zhuang, Z.; Cao, Z.; Du, H. Simple chiral chain dienes as ligands for Rh(I)-catalyzed conjugated additions. Org. Lett. 2009, 11, 4744-4747.
42. Li, Q.; Dong, Z.; Yu, Z.-X. a,ß-Divinyl terahydropyrroles as chiral chain diene ligands in rhodium(I)-catalyzed enantioselective conjugated additions. Org. Lett. 2011, 13, 1122-1125.
43. Liu, C.-C.; Janmanchi, D.; Chen, C.-C.; Wu, H.L. Expanding the C1-symmetric bicylo[2.2.1] heptadiene ligand family: Highly enantioselective synthesis of cyclic ß-Aryl-substituted carbonyl compounds. Eur. J. Org. Chem. 2012, 2012, 2503-2507.
44. Shi, Q.; Xu, L.; Li, X.; Jia, X.; Wang, R.; Au-Yeung, T.T.-L.; Chan, A.S.C.; Hayashi, T.; Cao, R.C.; Hong, M. Bipyridyl-based diphosphine as an efficient ligand in the rhodium-catalyzed asymmetric conjugate addition of arylboronic acids to a,ß-unsaturated ketones. Tetrahedron Lett. 2003, 55, 6505-6508.
45. Madec, J.; Michaud, G.; Genêt, J.-P.; Marinetti, A. New developments in the synthesis of heterotopic atropisomeric diphosphines via diastereoselective aryl coupling reactions. Tetrahedron: Asymmetry 2004, 15, 2253-2261.
46. Stemmler, R.T.; Bolm, C. Planar-chiral cyrhetrenes for the Rhodium-catalyzed asymmetric 1,4-Addition and the hydrogenation of enamides. J. Org. Chem. 2005, 70, 9925-9931.
47. Vandyck, K.; Matthys, B.; Willen, M.; Robeyns, K.; Meervelt, L.C.; der Eychen, J.V. Rhodium-catalyzed asymmetric conjugate additions of boronic acids to enones using DIPHONANE: A novel chiral bisphosphine ligand. Org. Lett. 2006, 8, 363-366.
48. Duan, W.-L.; Iwamura, H.; Shintani, R.; Hayashi, T. Chiral Phosphine-Olefin Ligands in the Rhodium-Catalyzed Asymmetric 1,4-Addition Reactions. J. Am. Chem. Soc. 2007, 129, 2130-2138.
49. Monti, C.; Gennari, C.; Piarulli, U. Rh-catalyzed enantioselective conjugate addition of arylboronic acids with a dynamic library of chiral tropos phosphorus ligands. Chem. Eur. J. 2007, 13, 1547-1558.
50. Mariz, R.; Luan, X.; Gatti, M.; Linden, A.; Dorta, R. A chiral bis-sulfoxide ligand in late-transition metal catalysis; rhodium-catalyzed asymmetric addition of arylboronic acids to electron-deficient olefins. J. Am. Chem. Soc. 2008, 130, 2172-2173.
51. Liao, Y.-X.; Xing, C.-H.; Israel, M.; Hu, Q.-S. Sequential aldol condensation-transition metal-catalyzed addition reactions of aldehydes, methyl ketones, and arylboronic acids. Org. Lett. 2011, 13, 2058-2061.
52. Wei, W.-T.; Yeh, J.-Y.; Kuo, T.-S.; Wu, H.-L. Highly enantioselective rhodium-catalyzed asymmetric 1,4-Addition reactions of arylboronic acids to acyclic a,ß-unsaturated compounds: The formal synthesis of (-)-Indatraline. Chem. Eur. J. 2011, 17, 11405-11409.
53. Yamamoto, Y.; Kurihara, K.; Sugishita, N.; Oshita, K.; Piao, D.; Miyaura, N. Chiral bis-phosphoramidites based on linked-BINOL for rhodium-catalyzed 1,4-Addition of arylboronic acids to a,ß-unsaturated carbonyl compounds. Chem. Lett. 2005, 34, 1224-1225.
54. Kurihara, K.; Sugishita, N.; Oshita, K.; Piao, D.; Yamamoto, Y.; Miyaura, N. Enantioselective 1,4-Addition of arylboronic acids to a,ß-unsaturated carbonyl compounds catalyzed by rhodium(I)-chiral phosphoramidite complexes. J. Organomet. Chem. 2007, 692, 428-435.
55. Majima, K.; Takita, R.; Okada, A.; Oshima, T.; Shibasaki, M. Catalytic asymmetric michael reaction of ß-keto esters: Effects of the linker heteroatom in linked-BINOL. J. Am. Chem. Soc. 2003, 125, 15837-15845.
56. Kurihra, K.; Yamamoto, Y.; Miyaura, N. An N-linked bidentate phosphoramidite ligand (N-Me-BIPAM) for Rhodium-catalyzed asymmetric addition of arylboronic acids to N-sulfonylarylaldimines. Adv. Synth. Catal. 2009, 351, 260-270.
57. Zacheis, D.; Dhar, A.; Lu, S.; Madler, M.M.; Klucik, J.; Brown, C.W.; Liu, S.; Clement, F.; Subramanian, S.; Weerasekare, G.M.; et al. Heteroarotinoids inhibit head and neck cancer cell lines in vitro and in vivo through both RAR and RXR retinoic acid receptors J. Med. Chem. 1999, 42, 4434-4445.
58. Nishikata, T.; Yamamoto, Y.; Miyaura, N. Palladium(II)-catalyzed 1,4-Addition of arylboronic acids to ß-Arylenones for enantioselective synthesis of 4-Aryl-4H-chromenes. Adv. Synth. Catal. 2007, 349, 1759-1764.
59. Itooka, R.; Iguchi, Y.; Miyaura, N. Rhodium-catalyzed 1,4-Addition of arylboronic acids to a,ß-unsaturated carbonyl compounds: Large accelerating effects of bases and ligands. J. Org. Chem. 2003, 68, 6000-6004.