Asymmetric synthesis of a tertiary arsine by nucleophilic addition to a chiral phosphine-stabilized arsenium salt

Organometallics

Volumn 27, Issue 19, 2008, Pages 5099-5107

  Coote, Michelle L ^a   Krenske, Elizabeth H ^a   Porter, Keith A ^a   Weir, Michelle L ^a   Willis, Anthony C ^a   Zhou, Xiangting ^a   Wild, S Bruce ^a  

^a AUSTRALIAN NATIONAL UNIVERSITY   (Australia)

Author keywords

[No Author keywords available]

Indexed keywords

ARGON; ARSENIC; COMPLEXATION; DICHLOROMETHANE; ELECTRON TRANSITIONS; ENANTIOSELECTIVITY; IONS; NUCLEAR MAGNETIC RESONANCE; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; OXYGEN; PHOSPHORUS; PHOSPHORUS COMPOUNDS; SEMICONDUCTING INDIUM GALLIUM ARSENIDE; SOLID SOLUTIONS; SULFUR COMPOUNDS;

ASYMMETRIC SYNTHESES; BOND DISSOCIATIONS; CHIRAL PHOSPHINES; CONSISTENT; DFT CALCULATIONS; DIASTEREOMER; DIASTEREOMERIC EXCESSES; DIASTEREOSELECTIVITY; DICHLOROMETHANE SOLUTIONS; ENANTIOMERIC EXCESSES; METHOXYMETHYL; MODEL COMPLEXES; NMR SPECTROSCOPIES; NUCLEOPHILIC ADDITIONS; PHENYL SUBSTITUENTS; S ENANTIOMERS; SOLID STATES; STEREODIFFERENTIATION; TERTIARY ARSINES;

COORDINATION REACTIONS;

EID: 54249122085     PISSN: 02767333     EISSN: None     Source Type: Journal    
DOI: 10.1021/om8006272     Document Type: Article

References (68)

1. (a) Horner, L.; Büthe, H.; Siegel, H. Tetrahedron Lett. 1968, 4023-4026.
2. (b) Horner, L.; Siegel, H.; Büthe, H. Angew. Chem., Int. Ed. Engl. 1968, 7, 942.
3. (c) Horner, L.; Siegel, H. Phosphorus Relat. Group V Elem. 1972, 1, 209-216.
4. (d) Knowles, W. S.; Sabacky, M. J. J. Chem. Soc., Chem. Commun. 1968, 1445.
5. (e) Knowles, W. S.; Sabacky, M. J.; Vineyard, B. D. J. Chem. Soc., Chem Commun. 1972, 10-11.
6. Knowles, W. S.; Sabacky, M. J.; Vineyard, B. D.; Weinkauff, D. J. J. Am. Chem. Soc. 1975, 97, 2567-2568.
7. (a) Dang, T. P.; Kagan, H. B. J. Chem. Soc., Chem. Commun. 1971, 481.
8. (b) Dang, T.; Kagan, H. J. Am. Chem. Soc. 1972, 6429-6433.
9. (c) Fryzuk, M. D.; Bosnich, B. J. Am. Chem. Soc. 1977, 99, 6262-6267.
10. (d) Fryzuk, M. D.; Bosnich, B. J. Am. Chem. Soc. 1978, 100, 5491-5494.
11. (a) Lagasse, F.; Kagan, H. B. Chem. Pharm. Bull. 2000, 48, 315-324.
12. (b) Crépy, K. V. L.; Imamoto, T. Top. Curr. Chem. 2003, 229, 1-40.
13. (a) Allen, D. G.; Wild, S. B.; Wood, D. L. Organometallics 1986, 5, 1009-1015.
14. (b) Mokhlesur Rahman, A. F. M. M.; Wild, S. B. J. Mol. Catal. 1987, 39, 155-160.
15. Pietrusiewicz, K. M.; Zablocka, M. Chem. Rev. 1994, 94, 1375-1411.
16. Wild, S. B. In The Chemistry of Organic Arsenic, Antimony and Bismuth Compounds; Patai, S., Ed.; John Wiley and Sons: Chichester, 1994; Chapter 3.
17. (a) Korpiun, O.; Mislow, K. J. Am. Chem. Soc. 1967, 89, 4784-4785.
18. (b) Korpiun, O.; Lewis, R. A.; Chickos, J.; Mislow, K. J. Am. Chem. Soc. 1968, 90, 4842-4846.
19. (c) Nudelman, A.; Cram, D. J. J. Am. Chem. Soc. 1968, 90, 3869-3870.
20. Stackhouse, J.; Cook, R. J.; Mislow, K. J. Am. Chem. Soc. 1973, 95, 953-955.
21. (a) Buhro, W. E.; Zwick, B. D.; Georgiou, S.; Hutchinson, J. P.; Gladysz, J. A. J. Am. Chem. Soc. 1988, 110, 2427-2439.
22. (b) Crisp, G. T.; Salem, G.; Wild, S. B. Organometallics 1989, 8, 2360-2367.
23. (c) Salem, G.; Wild, S. B. J. Organomet. Chem. 1989, 370, 33-41.
24. (d) Bohle, D. S.; Clark, G. R.; Rickard, C. E. F.; Roper, W. R. J. Organomet. Chem. 1990, 393, 243-285.
25. Moncarz, J. R.; Laritcheva, N. F.; Glueck, D. S. J. Am. Chem. Soc. 2002, 124, 13356-13357.
26. Scriban, C.; Glueck, D. S. J. Am. Chem. Soc. 2006, 128, 2788-2789.
27. Chan, V. S.; Stewart, I. C.; Bergman, R. G.; Toste, F. D. J. Am. Chem. Soc. 2006, 128, 2786-2787.
28. Wild, S. B. Coord. Chem. Rev. 1997, 166, 291-311.
29. 18
30. Horner, L.; Fuchs, H. Tetrahedron Lett. 1962, 203-204.
31. Horner, L.; Winkler, H.; Meyer, E. Tetrahedron Lett. 1965, 789-792.
32. Peerdeman, A. F.; Holst, J. P. C.; Horner, L.; Winkler, H. Tetrahedron Lett. 1965, 811-815.
33. (a) Porter, K. A.; Willis, A. C.; Zank, J.; Wild, S. B. Inorg. Chem. 2002, 41, 6380-6386.
34. (b) Burford, N.; Ragogna, P. J.; Sharp, K.; McDonald, R.; Ferguson, M. J. Inorg. Chem. 2005, 44, 9453-9460.
35. (a) Cahn, R. S.; Ingold, C. K.; Prelog, V. Angew. Chem., Int. Ed. Engl. 1966, 5, 385-415.
36. (b) Eliel, E. L.; Wilen, S. H.; Mander, L. N. Stereochemistry of Organic Compounds; John Wiley and Sons, Inc.: New York, 1994.
37. 22
38. Senkler, G. H.; Mislow, K. J. Am. Chem. Soc. 1972, 94, 291.
39. Asymmetric Catalysis; Bosnich, B., Ed.;NATO ASI Series; Martinus Nijhoff Publishers: Dordrecht, 1984.
40. (a) Gladiali, S.; Dore, A.; Fabbri, D.; De Lucchi, O.; Manassero, M. Tetrahedron: Asymmetry 1994, 5, 511-514.
41. (b) Junge, K.; Hagemann, B.; Enthaler, S.; Spannenberg, A.; Michalik, M.; Oehme, G.; Monsees, A.; Riermeir, T.; Beller, M. Tetrahedron: Asymmetry 2004, 15, 2621-2631.
42. Xiao, D.; Zhang, Z.; Zhang, X. Org. Lett. 1999, 1, 1679-1681.
43. Engelhart, L. M.; Leung, W. P.; Raston, C. L.; Salem, G.; Twiss, P.; White, A. H. J. Chem. Soc., Dalton Trans. 1988, 2403-2409.
44. Bondi, A. J. Phys. Chem. 1964, 68, 441-451.
45. (a) Bitterer, F.; Herd, O.; Kuhnel, M.; Stelzer, O.; Weferling, N.; Sheldrick, W.; Hahn, J.; Nagel, S.; Rosch, N. Inorg. Chem. 1998, 37, 6408-6417.
46. (b) Tang, W.; Wang, W.; Chi, Y.; Zhang, Z. Angew. Chem., Int. Ed. 2003, 42, 3509.
47. Grepioni, F.; Cojazzi, G.; Draper, S. M.; Scully, N.; Braga, D. Organometallics 1998, 17, 296-307.
48. Sanders, J. K. M.; Hunter, B. K. Modern NMR Spectroscopy, 2nd ed.; Oxford University Press: Oxford, 1993; Chapter 6.
49. (a) Roberts, N. K.; Wild, S. B. J. Chem. Soc., Dalton Trans. 1979, 2015-2021.
50. (b) Hockless, D. C. R.; Gugger, P. A.; Leung, P. H.; Mayadunne, R. C.; Pabel, M.; Wild, S. B. Tetrahedron 1997, 53, 4083-4094.
51. Köbrich, G.; Merkle, H. R. Chem. Ber. 1966, 99, 1782-1792.
52. Laidler, K. J.; Meiser, J. H. Physical Chemistry, 2nd ed.; Houghton Mifflin: Boston, 1995; pp 703-706.
53. Amarego, W. F. L.; Chai, C. L. L. Purification of Laboratory Chemicals, 5th ed.; Butterworth-Heinemann: Amsterdam, 2003.
54. Kilah, N. L.; Weir, M. L.; Wild, S. B. Dalton Trans. 2008, 2480-2486.
55. Kamai, G. Ber. Dtsch. Chem. Ges. 1935, 68B, 1893-1898.
56. Cragoe, E. J.; Andres, R. J.; Coles, R. F.; Elpern, B.; Morgan, J. F.; Hamilton, C. S. J. Am. Chem. Soc. 1947, 69, 925-926.
57. Otwinowski, Z.; Minor, W. Methods Enzymol. 1996, 276, 307-326.
58. Coppens, P. In Crystallographic Computing; Ahmed, F. R.; Hall, S. R., Huber, C. P., Eds.; Munksgaard: Copenhagen, 1970; pp 255-270.
59. Altomare, A.; Cascarano, G.; Giacovazzo, C.; Guagliardi, A.; Burla, M. C.; Polidori, G.; Camalli, M. J. Appl. Crystallogr. 1994, 27, 435.
60. Betteridge, P. W.; Carruthers, J. R.; Cooper, R. I.; Prout, K.; Watlan, D. J. J. Appl. Crystallogr. 2003, 36, 1487.
61. teXsan: Single-Crystal Structure Analysis Package, version 1.8; Molecular Structure Corporation: The Woodlands. TX, 1997.
62. Koch, W.; Holthausen, M. C. A Chemist's Guide to Density Functional Theory; Wiley-VCH: Weinheim, 2000.
63. Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R. ; Montgomery, J. A., Jr.; Vreven, T.; Kudin, K. N.; Burant, J. C.; Millam, J. M.; Iyengar, S. S.; Tomasi, J.; Barone, V.; Mennucci, B.; Cossi, M.; Scalmani, G.; Rega, N.; Petersson, G. A.; Nakatsuji, H.; Hada, M.; Ehara, M.; Toyota, K.; Fukuda, R.; Hasegawa, J.; Ishida, M.; Nakajima, T.; Honda, Y.; Kitao, O.; Nakai, H.; Klene, M.; Li, X.; Knox, J. E.; Hratchian, H. P.; Cross, J. B.; Bakken, V.; Adamo, C.; Jaramillo, J.; Gomperts, R.; Stratmann, R. E.; Yazyev, O.; Austin, A. J.; Cammi, R.; Pomelli, C.; Ochterski, J. W.; Ayala, P. Y.; Morokuma, K.; Voth, G. A.; Salvador, P.; Dannenberg, J. J.; Zakrzewski, V. G.; Dapprich, S.; Daniels, A. D.; Strain, M. C.; Farkas, O.; Malick, D. K.; Rabuck, A. D.; Raghavachari, K.; Foresman, J. B.; Ortiz, J. V.; Cui, Q.; Baboul, A. G.; Clifford, S.; Cioslowski, J.; Stefanov, B. B.; Liu, G.; Liashenko, A.; Piskorz, P.; Komaromi, I.; Martin, R. L.; Fox, D. J.; Keith, T.; Al-Laham, M. A.; Peng, C. Y.; Nanayakkara, A.; Challacombe, M.; Gill, P. M. W.; Johnson, B.; Chen, W.; Wong, M. W.; Gonzalez, C.; Pople, J. A. GAUSSIAN 03, Revision B.03; Gaussian Inc.: Wallingford, CT, 2004.
64. Kohn, W.; Becke, A. D.; Parr, R. G. J. Phys. Chem. 1996, 100, 12974-12980.
65. See for example: (a) Coote, M. L.; Wood, G. P. F.; Radom, L. J. Phys. Chem. A 2002, 106, 12124-12138.
66. (b) Gömez-Baldera, R.; Coote, M. L.; Henry, D. J.; Radom, L. J. Phys. Chem. A 2004, 108, 2874-2883.
67. Dunning, T. H., Jr.; Hay, P. J. In Modern Theoretical Chemistry; Schaefer, H. F., III, Ed.; Plenum: New York, 1976; Vol. 3, pp 1-28.
68. Scott, A. P.; Radom, L. J. Phys. Chem. 1996, 100, 16502-16513.