A Route to Carbasugar Analogues - Jonathan Clayden - The ...
A Route to Carbasugar Analogues - Jonathan Clayden - The ... A Route to Carbasugar Analogues - Jonathan Clayden - The ...
References (73) Betson, M. S.; Clayden, J.; Worrall, C. P.; Peace, S. Angew. Chem., Int. Ed. 2006, 45, 5803-5807. (74) Köbrich, G.; Buck, P. Chem. Ber. 1970, 103, 1412-1419. (75) Kolotuchin, S. V.; Meyers, A. I. J. Org. Chem. 2000, 65, 3018-3026. (76) Rathke, M. W.; Sullivan, D. Tetrahedron Lett. 1972, 13, 4249. (77) Pross, A. Acc. Chem. Res. 1985, 18, 212-219. (78) Eberson, L.; Shaik, S. S. J. Am. Chem. Soc. 1990, 112, 4484-4489. (79) Ashby, E. C. Acc. Chem. Res. 1988, 21, 414-421. (80) Ashby, E. C.; Pham, T. N. J. Org. Chem. 1987, 52, 1291-1300. (81) Newcomb, M.; Williams, W. G.; Crumpacker, E. L. Tetrahedron Lett. 1985, 26, 1183. (82) Bailey, W. F.; Patricia, J. J.; Nurmi, T. T.; Wang, W. Tetrahedron Lett. 1986, 27, 1861. (83) Meites, L.; Zuman, P. Electrochemical data; J. Wiley: New York, 1974. (84) Ashby, E. C.; Goel, A. B.; DePriest, R. N. J. Am. Chem. Soc. 1980, 102, 7779- 7780. (85) Gawley, R. E.; Low, E.; Zhang, Q.; Harris, R. J. Am. Chem. Soc. 2000, 122, 3344-3350. (86) Hoffmann, R. W. Chem. Soc. Rev. 2003, 32, 225-230. (87) Yamataka, H.; Sasaki, D.; Kuwatani, Y.; Mishima, M.; Shimizu, M.; Tsuno, Y. J. Org. Chem. 2001, 66, 2131-2135. (88) Clayden, J.; Knowles, F. E.; Baldwin, I. R. J. Am. Chem. Soc. 2005, 127, 2412- 2413. (89) Köhnlein, W.; Böddeker, K. W.; Schindewolf, U. Angew. Chem., Int. Ed. 1967, 6, 360-361. (90) X-band refers to the wavelength of the microwaves used to split the spin states (30 mm) (91) the modulation amplitude was too large to be able to observe the hyperfine couplings (92) Newcomb, M.; Curran, D. P. Acc. Chem. Res. 1988, 21, 206-214. (93) Carey, F. A.; Sundberg, R. J. Advanced Organic Chemistry Part A: Structure & Mechanism; Fourth ed.; Kluwer Academic, 2000. (94) Johnston, L. J.; Lusztyk, J.; Wayner, D. D. M.; Abeywickreyma, A. N.; Beckwith, A. L. J.; Scaiano, J. C.; Ingold, K. U. J. Am. Chem. Soc. 1985, 107, 4594-4596. (95) Goodman, J. M.; Kirby, P. D.; Haustedt, L. O. Tetrahedron Lett. 2000, 41, 9879. (96) Griller, D.; Ingold, K. U. Acc. Chem. Res. 1980, 13, 317-323. (97) Bailey, W. F.; Punzalan, E. R. Tetrahedron Lett. 1996, 37, 5435. (98) Still, W. C.; Macdonald, T. L. J. Am. Chem. Soc. 1974, 96, 5561-5563. (99) Clayden, J.; Kenworthy, M. N. Org. Lett. 2002, 4, 787-790. (100) Yamataka, H.; Fujimura, N.; Kawafuji, Y.; Hanafusa, T. J. Am. Chem. Soc. 1987, 109, 4305-4308. (101) Ashby, E. C.; Wiesemann, T. L. J. Am. Chem. Soc. 1978, 100, 3101-3110. (102) Yamataka, H.; Kawafuji, Y.; Nagareda, K.; Miyano, N.; Hanafusa, T. J. Org. Chem. 1989, 54, 4706-4708. (103) Yamataka, H.; Sasaki, D.; Kuwatani, Y.; Mishima, M.; Tsuno, Y. J. Am. Chem. Soc. 1997, 119, 9975-9979. (104) Yamataka, H.; Matsuyama, T.; Hanafusa, T. J. Am. Chem. Soc. 1989, 111, 4912-4918. 187
References (105) Gajewski, J. J.; Bocian, W.; Harris, N. J.; Olson, L. P.; Gajewski, J. P. J. Am. Chem. Soc. 1999, 121, 326-334. (106) Meyers, A. I.; Mihelich, E. D. J. Org. Chem. 1975, 40, 3158. (107) Hansch, C.; Leo, A.; Taft, R. W. Chem. Rev. 1991, 91, 165-195. (108) Hoffmann, R. W.; Holzer, B. Chem. Commun. 2001, 491-492. (109) Collum, D. B. Acc. Chem. Res. 1992, 25, 448-454. (110) Leung, S. S. W.; Streitwieser, A. J. Org. Chem. 1999, 64, 3390-3391. (111) Sikorski, W. H.; Reich, H. J. J. Am. Chem. Soc. 2001, 123, 6527-6535. (112) Reich, H. J.; Sikorski, W. H.; Gudmundsson, B. O.; Dykstra, R. R. J. Am. Chem. Soc. 1998, 120, 4035-4036. (113) Siemeling, U.; Redecker, T.; Neumann, B.; Stammler, H.-G. J. Am. Chem. Soc. 1994, 116, 5507-5508. (114) Minakata, S.; Nishimura, M.; Takahashi, T.; Oderaotoshi, Y.; Komatsu, M. Tetrahedron Lett. 2001, 42, 9019. (115) Ager, D. J.; Prakash, I.; Schaad, D. R. Chem. Rev. 1996, 96, 835-876. (116) Frump, J. A. Chem. Rev. 1971, 71, 483-505. (117) Greene, T. W.; Wuts, P. G. M. Protective Groups in Organic Synthesis; Third ed.; Wiley, 1999. (118) Crosignani, S.; Young, A. C.; Linclau, B. Tetrahedron Lett. 2004, 45, 9611- 9615. (119) Liu, H.; Xu, J.; Du, D. M. Org. Lett. 2007, 9, 4725-4728. (120) Heine, H. W.; Kaplin, M. S. J. Org. Chem. 1967, 36, 3069-74. (121) Ferraris, D.; Drury, W. J.; Cox, C.; Lectka, T. J. Org. Chem. 1998, 63, 4568- 4569. (122) Haidukewych, D.; Meyers, A. I. Tetrahedron Lett. 1972, 13, 3031. (123) Aggarwal, V. K.; Vasse, J.-L. Org. Lett. 2003, 5, 3987. (124) Kamata, K.; Agata, I.; Meyers, A. I. J. Org. Chem. 1998, 63, 3113-3116. (125) Witte, H.; Seeliger, W. Liebigs Ann. Chem. 1974, 1974, 996-1009. (126) Chang, H.-T.; Sharpless, K. B. Tetrahedron Lett. 1996, 37, 3219. (127) Lipshutz, B. H.; Miller, T. A. Tetrahedron Lett. 1990, 31, 5253. (128) Murray, R. W.; Singh, M. Org. Synth. 1998, Coll. Vol. 9, 288. (129) Lygo, B., Suggestion to use diethyl ether-petrol solvent at low temperature to encourage precipitation of Et 3 N.HCl salt, reducing free chloride ions which would otherwise attack the aziridine ring. (130) Harvey, R. A.; University of Manchester: 2006-2008. (131) Sigma-Aldrich, As of Apr 2008: both (1R,2R)-(+)-2-Amino-1,2- diphenylethanol (CAS 88082-66-0, catalogue no. 671126), and (1S,2S)-(−)-2- Amino-1,2-diphenylethanol (CAS 23190-16-1, catalogue no. 671223) are available at £43.50 / 0.5g. (132) Meyers, A. I.; Temple, D. L.; Haidukewych, D.; Mihelich, E. D. J. Org. Chem. 1974, 39, 2787-2793. (133) Meyers, A. I.; Knaus, G.; Kamata, K. J. Am. Chem. Soc. 1974, 96, 268-270. (134) Meyers, A. I.; Slade, J. J. Org. Chem. 1980, 45, 2785-2791. (135) Toxicitiy of methyl triflate is comparable with "Magic Methyl" (methyl fluorosulfonate) whose vapours have proven deadly. See next reference. (136) Stiles, D. In Chemistry World 2007; Vol. 4. (137) Meyers, A. I.; Himmelsbach, R. J.; Reuman, M. J. Org. Chem. 1983, 48, 4053- 4058. (138) Pridgen, L. N.; Killmer, L. B.; Webb, R. L. J. Org. Chem. 1982, 47, 1985- 1989. 188
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References<br />
(105) Gajewski, J. J.; Bocian, W.; Harris, N. J.; Olson, L. P.; Gajewski, J. P. J. Am.<br />
Chem. Soc. 1999, 121, 326-334.<br />
(106) Meyers, A. I.; Mihelich, E. D. J. Org. Chem. 1975, 40, 3158.<br />
(107) Hansch, C.; Leo, A.; Taft, R. W. Chem. Rev. 1991, 91, 165-195.<br />
(108) Hoffmann, R. W.; Holzer, B. Chem. Commun. 2001, 491-492.<br />
(109) Collum, D. B. Acc. Chem. Res. 1992, 25, 448-454.<br />
(110) Leung, S. S. W.; Streitwieser, A. J. Org. Chem. 1999, 64, 3390-3391.<br />
(111) Sikorski, W. H.; Reich, H. J. J. Am. Chem. Soc. 2001, 123, 6527-6535.<br />
(112) Reich, H. J.; Sikorski, W. H.; Gudmundsson, B. O.; Dykstra, R. R. J. Am.<br />
Chem. Soc. 1998, 120, 4035-4036.<br />
(113) Siemeling, U.; Redecker, T.; Neumann, B.; Stammler, H.-G. J. Am. Chem. Soc.<br />
1994, 116, 5507-5508.<br />
(114) Minakata, S.; Nishimura, M.; Takahashi, T.; Oderao<strong>to</strong>shi, Y.; Komatsu, M.<br />
Tetrahedron Lett. 2001, 42, 9019.<br />
(115) Ager, D. J.; Prakash, I.; Schaad, D. R. Chem. Rev. 1996, 96, 835-876.<br />
(116) Frump, J. A. Chem. Rev. 1971, 71, 483-505.<br />
(117) Greene, T. W.; Wuts, P. G. M. Protective Groups in Organic Synthesis; Third<br />
ed.; Wiley, 1999.<br />
(118) Crosignani, S.; Young, A. C.; Linclau, B. Tetrahedron Lett. 2004, 45, 9611-<br />
9615.<br />
(119) Liu, H.; Xu, J.; Du, D. M. Org. Lett. 2007, 9, 4725-4728.<br />
(120) Heine, H. W.; Kaplin, M. S. J. Org. Chem. 1967, 36, 3069-74.<br />
(121) Ferraris, D.; Drury, W. J.; Cox, C.; Lectka, T. J. Org. Chem. 1998, 63, 4568-<br />
4569.<br />
(122) Haidukewych, D.; Meyers, A. I. Tetrahedron Lett. 1972, 13, 3031.<br />
(123) Aggarwal, V. K.; Vasse, J.-L. Org. Lett. 2003, 5, 3987.<br />
(124) Kamata, K.; Agata, I.; Meyers, A. I. J. Org. Chem. 1998, 63, 3113-3116.<br />
(125) Witte, H.; Seeliger, W. Liebigs Ann. Chem. 1974, 1974, 996-1009.<br />
(126) Chang, H.-T.; Sharpless, K. B. Tetrahedron Lett. 1996, 37, 3219.<br />
(127) Lipshutz, B. H.; Miller, T. A. Tetrahedron Lett. 1990, 31, 5253.<br />
(128) Murray, R. W.; Singh, M. Org. Synth. 1998, Coll. Vol. 9, 288.<br />
(129) Lygo, B., Suggestion <strong>to</strong> use diethyl ether-petrol solvent at low temperature <strong>to</strong><br />
encourage precipitation of Et 3 N.HCl salt, reducing free chloride ions which<br />
would otherwise attack the aziridine ring.<br />
(130) Harvey, R. A.; University of Manchester: 2006-2008.<br />
(131) Sigma-Aldrich, As of Apr 2008: both (1R,2R)-(+)-2-Amino-1,2-<br />
diphenylethanol (CAS 88082-66-0, catalogue no. 671126), and (1S,2S)-(−)-2-<br />
Amino-1,2-diphenylethanol (CAS 23190-16-1, catalogue no. 671223) are<br />
available at £43.50 / 0.5g.<br />
(132) Meyers, A. I.; Temple, D. L.; Haidukewych, D.; Mihelich, E. D. J. Org. Chem.<br />
1974, 39, 2787-2793.<br />
(133) Meyers, A. I.; Knaus, G.; Kamata, K. J. Am. Chem. Soc. 1974, 96, 268-270.<br />
(134) Meyers, A. I.; Slade, J. J. Org. Chem. 1980, 45, 2785-2791.<br />
(135) Toxicitiy of methyl triflate is comparable with "Magic Methyl" (methyl<br />
fluorosulfonate) whose vapours have proven deadly. See next reference.<br />
(136) Stiles, D. In Chemistry World 2007; Vol. 4.<br />
(137) Meyers, A. I.; Himmelsbach, R. J.; Reuman, M. J. Org. Chem. 1983, 48, 4053-<br />
4058.<br />
(138) Pridgen, L. N.; Killmer, L. B.; Webb, R. L. J. Org. Chem. 1982, 47, 1985-<br />
1989.<br />
188
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