Hydroxamic acids in asymmetric synthesis

Accounts of Chemical Research

Volumn 46, Issue 2, 2013, Pages 506-518

  Li, Zhi ^a   Yamamoto, Hisashi ^a  

^a UNIVERSITY OF CHICAGO   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EPOXIDE; HYDROXAMIC ACID; VANADIUM;

ARTICLE; CATALYSIS; CHEMISTRY; STEREOISOMERISM;

CATALYSIS; EPOXY COMPOUNDS; HYDROXAMIC ACIDS; STEREOISOMERISM; VANADIUM;

EID: 84874103827     PISSN: 00014842     EISSN: 15204898     Source Type: Journal    
DOI: 10.1021/ar300216r     Document Type: Article

References (55)

1. Rouhi, A. M. Chiral Chemistry Chem. Eng. News 2004, 47-62
2. Bauer, E. B. Chiral-at-metal complexes and their catalytic applications in organic synthesis Chem. Soc. Rev. 2012, 41 (8) 3153-3167
3. Yoon, T. P.; Jacobsen, E. N. Privileged Chiral Catalysts Science 2003, 299 (5613) 1691-1693
4. Codd, R. Traversing the coordination chemistry and chemical biology of hydroxamic acids Coord. Chem. Rev. 2008, 252 (12-14) 1387-1408
5. Matlin, S. A.; Sammes, P. G.; Upton, R. M. The oxidation of trimethylsilylated amides to hydroxamic acids J. Chem. Soc., Perkin Trans. 1 1979, 2481-2487
6. Wong, F. T.; Patra, P. K.; Seayad, J.; Zhang, Y.; Ying, J. Y. N-Heterocyclic Carbene (NHC)-Catalyzed Direct Amidation of Aldehydes with Nitroso Compounds Org. Lett. 2008, 10 (12) 2333-2336
7. Michaelson, R. C.; Palermo, R. E.; Sharpless, K. B. Chiral hydroxamic acids as ligands in the vanadium catalyzed asymmetric epoxidation of allylic alcohols by tert-butyl hydroperoxide J. Am. Chem. Soc. 1977, 99 (6) 1990-1992
8. Sharpless, K. B.; Verhoeven, T. R. Metal-Catalyzed, Highly Selective Oxygenations of Olefins and Acetylenes with tert -Butyl Hydroperoxide. Practical Considerations and Mechanisms Aldrichim. Acta 1979, 12, 63-73
9. Berrisford, D. J.; Bolm, C.; Sharpless, K. B. Ligand-Accelerated Catalysis Angew. Chem., Int. Ed. Engl. 1995, 34 (10) 1059-1070
10. Katsuki, T.; Sharpless, K. B. The first practical method for asymmetric epoxidation J. Am. Chem. Soc. 1980, 102, 5974-5976
11. Gao, Y.; Klunder, J. M.; Hanson, R. M.; Masamune, H.; Ko, S. Y.; Sharpless, K. B. Catalytic asymmetric epoxidation and kinetic resolution: modified procedures including in situ derivatization J. Am. Chem. Soc. 1987, 109, 5765-5780
12. Katsuki, T.; Martin, V. S. Asymmetric Epoxidation of Allylic Alcohols: the Katsuki-Sharpless Epoxidation Reaction Org. React. 1996, 48, 1-299
13. Murase, N.; Hoshino, Y.; Oishi, M.; Yamamoto, H. Chiral Vanadium-Based Catalysts for Asymmetric Epoxidation of Allylic Alcohols J. Org. Chem. 1999, 64, 338-339
14. Hoshino, Y.; Murase, N.; Oishi, M.; Yamamoto, H. Design of Optically Active Hydroxamic Acids as Ligands in Vanadium-Catalyzed Asymmetric Epoxidation Bull. Chem. Soc. Jpn. 2000, 73 (7) 1653-1658
15. Hoshino, Y.; Yamamoto, H. Novel α-Amino Acid-Based Hydroxamic Acid Ligands for Vanadium-Catalyzed Asymmetric Epoxidation of Allylic Alcohols J. Am. Chem. Soc. 2000, 122, 10452-10453
16. Makita, N.; Hoshino, Y.; Yamamoto, H. Asymmetric Epoxidation of Homoallylic Alcohols and Application in a Concise Total Synthesis of (-)-α-Bisabolol and (-)-8-epi-α-Bisabolol Angew. Chem., Int. Ed. 2003, 42, 941-943
17. Zhang, W.; Basak, A.; Kosugi, Y.; Hoshino, Y.; Yamamoto, H. Enantioselective Epoxidation of Allylic Alcohols by a Chiral Complex of Vanadium: An Effective Controller System and a Rational Mechanistic Model Angew. Chem., Int. Ed. 2005, 44, 4389-4391
18. Zhang, W.; Yamamoto, H. Vanadium-Catalyzed Asymmetric Epoxidation of Homoallylic Alcohols J. Am. Chem. Soc. 2007, 129, 286-287
19. Schreiber, S. L.; Schreiber, T. S.; Smith, D. B. Reactions that proceed with a combination of enantiotopic group and diastereotopic face selectivity can deliver products with very high enantiomeric excess: experimental support of a mathematical model J. Am. Chem. Soc. 1987, 109 (5) 1525-1529
20. Li, Z.; Zhang, W.; Yamamoto, H. Vanadium-Catalyzed Enantioselective Desymmetrization of meso -Secondary Allylic Alcohols and Homoallylic Alcohols Angew. Chem., Int. Ed. 2008, 47 (39) 7520-7522
21. Smith, D. B.; Wang, Z.; Schreiber, S. L. The asymmetric epoxidation of divinyl carbinols: theory and applications Tetrahedron 1990, 46 (13-14) 4793-4808
22. Brückner, R., Asymmetric Epoxidation of Pentadienols. In Asymmetric Synthesis: The Essentials, 2 nd, completely revised ed.; Christmannqq, M.; Bräse, S., Eds. Wiley-VCH Verlag GmbH & Co.: Weinheim, Germany, 2008; pp 10-16.
23. Butler, D. E.; Deering, C. F.; Millar, A.; Nanninga, T. N.; Roth, B. D. Process for trans-6-[2-(substituted-pyrrol-1-yl)alkyl]pyran-2-one inhibitors of cholesterol synthesis. U.S. Patent 5,245,047, 1993.
24. Kocieński, P. J.; Yeates, C.; Street, S. D. A.; Campbell, S. F. The 3,4-dihydro-2H-pyran approach to (+)-milbemycin β3. Part 1. An alternative synthesis of (2S,4S,6R,8R,9S)-2-formylmethyl-4-(dimethyl-t- butylsilyloxy)-8,9-dimethyl-1,7-dioxaspiro[5.5]undecane J. Chem. Soc., Perkin Trans. 1 1987, 2183-2187
25. Kim, Y.-J.; Tae, J. Resolution of 2-Silyloxy-1-oxiranyl-4-pentenes by HKR: Total Synthesis of (5S,7R)-Kurzilactone Synlett 2006, 1, 61-64
26. Barlan, A. U.; Zhang, W.; Yamamoto, H. Development and application of versatile bis-hydroxamic acids for catalytic asymmetric oxidation Tetrahedron 2007, 63, 6075-6087
27. Bolm, C. Vanadium-catalyzed asymmetric oxidations Coord. Chem. Rev. 2003, 237, 245-256
28. Xia, Q. H.; Ge, H. Q.; Ye, C. P.; Liu, Z. M.; Su, K. X. Advances in Homogeneous and Heterogeneous Catalytic Asymmetric Epoxidation Chem. Rev. 2005, 105 (5) 1603-1662
29. Licini, G.; Conte, V.; Coletti, A.; Mba, M.; Zonta, C. Recent advances in vanadium catalyzed oxygen transfer reactions Coord. Chem. Rev. 2011, 255 (19-20) 2345-2357
30. da Silva, J. A. L.; da Silva, J. J. R. F.; Pombeiro, A. J. L. Oxovanadium complexes in catalytic oxidations Coord. Chem. Rev. 2011, 255 (19-20) 2232-2248
31. Barlan, A. U.; Basak, A.; Yamamoto, H. Enantioselective Oxidation of Olefins Catalyzed by a Chiral Bishydroxamic Acid Complex of Molybdenum Angew. Chem., Int. Ed. 2006, 45 (35) 5849-5852
32. Corey, E. J.; Noe, M. C.; Wen-Chung, S. A short and convergent enantioselective synthesis of (3S)-2,3-oxidosqualene Tetrahedron Lett. 1993, 34 (38) 5995-5998
33. Raina, S.; Singh, V. K. Reaction of epoxides with activated DMSO reagent. General method for synthesis of α-chlorocarbonyl compounds: Application in asymmetric synthesis of (3S)-2,3-oxidosqualene Tetrahedron 1995, 51 (8) 2467-2476
34. Brito, J. A.; Royo, B.; Gomez, M. An overview of chiral molybdenum complexes applied in enantioselective catalysis Catal. Sci. Technol. 2011, 1 (7) 1109-1118
35. Deubel, D. V.; Frenking, G.; Gisdakis, P.; Herrmann, W. A.; Rösch, N.; Sundermeyer, J. Olefin Epoxidation with Inorganic Peroxides. Solutions to Four Long-Standing Controversies on the Mechanism of Oxygen Transfer Acc. Chem. Res. 2004, 37 (9) 645-652
36. Basak, A.; Barlan, A. U.; Yamamoto, H. Catalytic enantioselective oxidation of sulfides and disulfides by a chiral complex of bis-hydroxamic acid and molybdenum Tetrahedron: Asymmetry 2006, 17 (4) 508-511
37. Jørgensen, K. A. Transition-metal-catalyzed epoxidations Chem. Rev. 1989, 89 (3) 431-458
38. Rossiter, B. E.; Sharpless, K. B. Asymmetric epoxidation of homoallylic alcohols. Synthesis of (-)-.gamma.-amino-.beta.-(R)-hydroxybutyric acid (GABOB) J. Org. Chem. 1984, 49, 3707-3711
39. Ikegami, S.; Katsuki, T.; Yamaguchi, M. Asymmetric Epoxidation of Homoallylic Alcohols Using Zirconium Tetrapropoxide, Dicyclohexyltartramide, and t-Butyl Hydroperoxide System Chem. Lett. 1987, 83-84
40. Okachi, T.; Murai, N.; Onaka, M. Catalytic Enantioselective Epoxidation of Homoallylic Alcohols by Chiral Zirconium Complexes Org. Lett. 2003, 5 (1) 85-87
41. Li, Z.; Yamamoto, H. Zirconium(IV)- and Hafnium(IV)-Catalyzed Highly Enantioselective Epoxidation of Homoallylic and Bishomoallylic Alcohols J. Am. Chem. Soc. 2010, 132, 7878-7880
42. Fouché, K. F.; le Roux, H. J.; Phillips, F. Complex formation of Zr(IV) and Hf(IV) with hydroxamic acids in acidic solutions J. Inorg. Nucl. Chem. 1970, 32, 1949-1962
43. Vogl, E. M.; Gröger, H.; Shibasaki, M. Towards Perfect Asymmetric Catalysis: Additives and Cocatalysts Angew. Chem., Int. Ed. 1999, 38 (11) 1570-1577
44. Hanson, R. M.; Sharpless, K. B. Procedure for the catalytic asymmetric epoxidation of allylic alcohols in the presence of molecular sieves J. Org. Chem. 1986, 51 (10) 1922-1925
45. Shannon, R. Revised effective ionic radii and systematic studies of interatomic distances in halides and chalcogenides Acta Crystallogr., Sect. A 1976, 32 (5) 751-767
46. -]: insertion and oxygen atom transfer J. Am. Chem. Soc. 1987, 109, 424-435
47. Li, Z. New Asymmetric Epoxidation Reactions Enabled by Chiral Metal-Bishydroxamic Acid Catalysts; Ph.D. Thesis, The University of Chicago, Chicago, IL, 2011.
48. Hoveyda, A. H.; Evans, D. A.; Fu, G. C. Substrate-directable chemical reactions Chem. Rev. 1993, 93 (4) 1307-1370
49. Olivares-Romero, J. L.; Li, Z.; Yamamoto, H. Hf(IV)-Catalyzed Enantioselective Epoxidation of N-Alkenyl Sulfonamides and N-Tosyl Imines J. Am. Chem. Soc. 2012, 134 (12) 5440-5443
50. Tsui, G. C.; Lautens, M. Linear-Selective Rhodium(I)-Catalyzed Addition of Arylboronic Acids to Allyl Sulfones Angew. Chem., Int. Ed. 2010, 49 (47) 8938-8941
51. Csatayová, K.; Davies, S. G.; Lee, J. A.; Ling, K. B.; Roberts, P. M.; Russell, A. J.; Thomson, J. E. Chemo- and diastereoselective cyclopropanation of allylic amines and carbamates Tetrahedron 2010, 66 (43) 8420-8440
52. Lykke, L.; Rodríguez-Escrich, C.; Jørgensen, K. A. Catalytic Enantioselective Oxaziridination J. Am. Chem. Soc. 2011, 133 (38) 14932-14935
53. Ahlford, K.; Ekström, J.; Zaitsev, A. B.; Ryberg, P.; Eriksson, L.; Adolfsson, H. Asymmetric Transfer Hydrogenation of Ketones Catalyzed by Amino Acid Derived Rhodium Complexes: On the Origin of Enantioselectivity and Enantioswitchability Chem.-Eur. J. 2009, 15 (42) 11197-11209
54. Ahlford, K.; Adolfsson, H. Amino acid derived amides and hydroxamic acids as ligands for asymmetric transfer hydrogenation in aqueous media Catal. Commun. 2011, 12 (12) 1118-1121
55. Binanzer, M.; Hsieh, S.-Y.; Bode, J. W. Catalytic Kinetic Resolution of Cyclic Secondary Amines J. Am. Chem. Soc. 2011, 133 (49) 19698-19701