Iodine monochloride-amine complexes: An experimental and computational approach to new chiral electrophiles

Chemistry - A European Journal

Volumn 11, Issue 19, 2005, Pages 5777-5785

  Haas, Jürgen ^a   Bissmire, Stewart ^a   Wirth, Thomas ^a  

^a CARDIFF UNIVERSITY   (United Kingdom)

Author keywords

Computer chemistry; Electrophiles; Iodine; Iodolactonization; Stereoselective synthesis

Indexed keywords

IODINE COMPOUNDS; MOLECULAR STRUCTURE; OLEFINS; ORGANIC ACIDS; STEREOCHEMISTRY; SYNTHESIS (CHEMICAL);

COMPUTER CHEMISTRY; ELECTROPHILES; IODOLACTONIZATION; STEREOSELECTIVE SYNTHESIS;

AMINES;

EID: 25444442832     PISSN: 09476539     EISSN: None     Source Type: Journal    
DOI: 10.1002/chem.200500507     Document Type: Review

References (49)

1. a) T. Wirth, Angew. Chem. 2000, 112, 3890-3900;
2. Angew. Chem. Int. Ed. 2000, 39, 3742-3751;
3. b) S. S. Khokhar, T. Wirth, Angew. Chem. 2004, 116, 641-643;
4. Angew. Chem. Int. Ed. 2004, 43, 631-633.
5. U. H. Hirt, M. F. H. Schuster, A. N. French, O. G. Wiest, T. Wirth, Eur. J. Org. Chem. 2001, 1569-1579.
6. a) M. D. Dowle, D. I. Davies, Chem. Soc. Rev. 1979, 8, 171;
7. b) K. E. Harding, T. H. Tiner in Comprehensive Organic Synthesis, Vol. 4, (Eds.: B. M. Trost, I. Fleming), Pergamon, Oxford, 1991, p. 363;
8. c) J. Mulzer in Organic Synthesis Highlights (Eds.: J. Mulzer, H. J. Altenbach, M. Braun, K. Krohn, H. U. Reissig), VCH, Weinheim, 1991, p. 157;
9. d) G. Rousseau, S. Robin, Tetrahedron 1998, 54, 13681-13736;
10. e) A. N. French, S. Bissmire, T. Wirth, Chem. Soc. Rev. 2004, 33, 354-362.
11. A. M. Lamsabhi, W. Bouab, M. Esseffar, M. Alcamí, M. Yáñez, J.L. M. Abboud, New J. Chem. 2001, 25, 509-517.
12. S. Santini, S. Sorriso, J. Chem. Soc. Faraday Trans. 1 1982, 78, 3153-3161.
13. A. K. Chandra, D. C. Mukherjee, Trans. Faraday Soc. 1964, 60, 6271.
14. J. Haas, S. Piguel, T. Wirth, Org. Lett. 2002, 4, 297-300.
15. R. B. Grossman, R. J. Trupp, Can. J. Chem. 1998, 76, 1233-1237.
16. R. S. Brown, X. L. Cui, J. Org. Chem. 2000, 65, 5653-5658.
17. S. H. Kang, S. B. Lee, C. M. Park, J. Am. Chem. Soc. 2003, 125, 15748-15749.
18. M. Wang, L. X. Gao, W. P. Mai, A. X. Xia, F. Wang, S. B. Zhang, J. Org. Chem. 2004, 69, 2875-2876.
19. 13NICl: C 38.80, H 4.23, N 4.52; found: C 38.58, H 4.23, N 4.44.
20. Similar results were obtained by using amine 4 for the UV/Vis experiment (isosbestic points at 231 and 286 nm).
21. After two equivalents of 4 were used to preform the complex with ICI, one equivalent of 3 was added at -78 C and the reaction was performed at -78°C, which resulted in a selectivity of 15% ee (S)-2, instead of the expected 12% ee (S)-2. Reversing the order of the amines (first 3, then 4) resulted in 2 % ee (R)-2.
22. The geometries of all species were obtained by conducting conformational analysis, optimized with no constraints, and the correct number of eigenvalues was confirmed by performing frequency calculations. Charges are given in elementary charge units, e. All calculations were performed by using Gaussian 98 (Revision A.11.1), M. J. Frisch, G. W. Trucks, H. B. Schlegel, G. E. Scuseria, M. A. Robb, J. R. Cheeseman, V. G. Zakrzewski, J. A. Montgomery, Jr., R. E. Stratmann, J. C. Burant, S. Dapprich, J. M. Millam, A. D. Daniels, K. N. Kudin, M. C. Strain, O. Farkas, J. Tomasi, V. Barone, M. Cossi, R. Cammi, B. Mennucci, C. Pomelli, C. Adamo, S. Clifford, J. Ochterski, G. A. Petersson, P. Y. Ayala, Q. Cui, K. Morokuma, P. Salvador, J. J. Dannenberg, D. K. Malick, A. D. Rabuck, K. Raghavachari, J. B. Foresman, J. Cioslowski, J. V. Ortiz, A. G. Baboul, B. B. Stefanov, G. Liu, A. Liashenko, P. Piskorz, I. Komaromi, R. Gomperts, R. L. Martin, D. J. Fox, T. Keith, M. A. Al-Laham, C. Y. Peng, A. Nanayakkara, M. Challacombe, P. M. W. Gill, B. Johnson, W. Chen, M. W. Wong, J. L. Andres, C. Gonzalez, M. Head-Gordon, E. S. Replogle, J. A. Pople, Gaussian, Inc., Pittsburgh PA, 2001.
23. T. R. Cundari, M. T. Benson, M. L. Lutz, S. O. Sommerer, Rev. Comput. Chem. 1996, 8, 145-202.
24. T. Leininger, A. Nicklass, H. Stoll, M. Dolg, P. Schwerdtfeger, J. Chem. Phys. 1996, 105, 1052-1059.
25. L. A. Curtiss, M. P. McGrath, J.-P. Blaudeau, N. E. Davis, R. C. Binning, Jr., L. Radom, J. Chem. Phys. 1995, 103, 6104-6113.
26. A. C. Legon, Chem. Phys. Lett. 1999, 314, 472-480.
27. a) A. E. Reed, L. A. Curtiss, F. Weinhold, Chem. Rev. 1988, 85, 899-926;
28. b) F. Weinhold in Encyclopedia of Computational Chemistry, Vol. 3, (Eds.: P. v. Schleyer, N. L. Allinger, P. A. Kollmann, T. Clark, H. F. Schaefer, J. J. Gasteiger, P. R. Schreinerpp, Wiley-VCH, Chichester, 1998, pp. 1792-1799.
29. C. S. Pomelli, J. Tomasi, M. Cossi, V. Barone, J. Comput. Chem. 1999, 20, 1693-1701.
30. J. Uenishi, M. Hamada, Synthesis 2002, 625-630.
31. a) E. N. Jacobsen, W. Zhang, M. L. Guler, J. Am. Chem. Soc. 1991, 113, 6703-6704;
32. b) D. Yang, Y.-C. Yip, J. Chen, K. K. Cheung, J. Am. Chem. Soc. 1998, 120, 7659-7660;
33. c) D. W. Nelson A. Gypser, P. T. Ho, H. C. Kolb, T. Kondo, H.-L. Kwong, D. V. McGrath, A. E. Rubin, P.-O. Norrby, K. P. Gable, K. B. Sharpless, J. Am. Chem. Soc. 1997, 119, 1840-1858;
34. d) C. M. Garner, S. Chiang, M. Nething, R. Monestel, Tetrahedron Lett. 2002, 43, 8339-8342.
35. a) C. Hansch, A. Leo, R. Taft, Chem. Rev. 1991, 91, 165-195;
36. b) N. Isaacs in Physical Organic Chemistry, 2nd ed., Longman Scientific and Technical, Essex, 1995.
37. p.
38. H.-S. Moon, S. W. E. Eisenberg, M. E. Wilson, N. E. Schore, M. J. Kurth, J. Org. Chem. 1994, 59, 6504-6505.
39. G. D. Harris, R. J. Herr, S. M. Weinreb, J. Org. Chem. 1993, 58, 5452-5464.
40. T. L. Gilchrist, P. D. Kemmitt, A. L. Germain, Tetrahedron 1997, 53, 4447-4456.
41. S. Handa, K. Jones, C. G. Newton, Tetrahedron Lett. 1988, 29, 3841-3844.
42. X. Verdaguer, U. E. W. Lange, M. T. Reding, S. L. Buchwald, J. Am. Chem. Soc. 1996, 118, 6784-6785.
43. G. van Koten, J. T. B. H. Jastrzebski, J. G. Noltes, W. M. G. F. Pontenagel, J. Kroon, A. L. J. Spek, J. Am. Chem. Soc. 1978, 100, 5021-5028.
44. B. M. Chanda, R. Vyas, A. V. Bedekar, J. Org. Chem. 2001, 66, 3034.
45. L. Uehlin, G. Fragale, T. Wirth, Chem. Eur. J. 2002, 8, 1125-1133.
46. W. Vaccaro, C. Amore, J. Berger, R. Burrier, J. Clader, H. Davis, M. Domalski, T. Fevig, B. Salisbury, R. Sher, J. Med. Chem. 1996, 39, 1704-1719.
47. S. Huggenberg, M. Hesse, Helv. Chim. Acta 1980, 63, 2295-2301.
48. R. W. Jackson, Tetrahedron Lett. 2001, 42, 5163-5165.
49. C. S. Foote, R. W. Denny, J. Am. Chem. Soc. 1971, 93, 5162-5167.