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 (139) Yoon, Y.-J.; Joo, J.-E.; Lee, K.-Y.; Kim, Y.-H.; Oh, C.-Y.; Ham, W.-H. Tetrahedron Lett. 2005, 46, 739. (140) Chen, Y.-J.; Lei, F.; Liu, L.; Wang, D. Tetrahedron 2003, 59, 7609. (141) Li, Y.; Manickam, G.; Ghoshal, A.; Subramaniam, P. Synth. Commun. 2006, 36, 925 - 928. (142) Clayden, J.; Dufour, J.; Grainger, D. M.; Helliwell, M. J. Am. Chem. Soc. 2007, 129, 7488-7489. (143) Kiessling, A. J.; McClure, C. K. Synth. Commun. 1997, 27, 923-937. (144) Johansen, M.; Bundgaard, H. J. Pharm. Sci. 1983, 72, 1294-1298. (145) Buur, A.; Bundgaard, H. Int. J. Pharm. 1984, 18, 325. (146) estimated as 6 x half-life of oxazolidine derived from pivalaldehyde and ephedrine, adjusted for ambient temperature (20 ºC drop in temperature gives c. four-fold decrease in reaction rate (147) Fife, T. H.; Hutchins, J. E. C. J. Org. Chem. 1980, 45, 2099-2104. (148) Walker, R. B.; Huang, M.-J.; Leszczynski, J. J. Mol. Struct. Theochem 2001, 549, 137. (149) Sigma-Aldrich, As of Apr 2008: (1S,2R)-(+)-2-Amino-1,2-diphenylethanol (CAS 23364-44-5) Sigma-Aldrich 331880, £21.50 / 1g; (1R,2S)-(−)-2-Amino- 1,2-diphenylethanol (CAS 23190-16-1) Sigma-Aldrich 331899 £36 for 1g. (150) McCasland, G. E.; Furuta, S.; Durham, L. J. J. Org. Chem. 1966, 31, 1516- 1521. (151) McCasland, G. E.; Furuta, S.; Durham, L. J. J. Org. Chem. 1968, 33, 2841- 2844. (152) Miwa, I.; Hara, H.; Okuda, J.; Suami, T.; Ogawa, S. Biochem. Int. 1985, 11, 809-16. (153) Miller, T. W.; Arison, B. H.; Albers-Schonberg, G. Biotechnol. Bioeng. 1973, 15, 1075-1080. (154) Marco-Contelles, J. Eur. J. Org. Chem. 2001, 2001, 1607-1618. (155) Chen, X.; Fan, Y.; Zheng, Y.; Shen, Y. Chem. Rev. 2003, 103, 1955-1978. (156) Arjona, O.; Gomez, A. M.; Lopez, J. C.; Plumet, J. Chem. Rev. 2007, 107, 1919-2036. (157) Johansson, L.; Lindskog, A.; Silfversparre, G.; Cimander, C.; Nielsen, K. F.; Lidén, G. Biotech. Bioeng. 2005, 92, 541-552. (158) Bradley, D. Nat. Rev. Drug Discov. 2005, 4, 945. (159) Acros Organics quote £31 for 100 mg, vs. £14 for 100 g for myo-inositol (Feb 2008) (160) Ogawa, S.; Ara, M.; Kondoh, T.; Saitoh, M.; Masuda, R.; Toyokami, T.; Suami, T. Bull. Chem. Soc. Jpn. 1980, 53, 1121. (161) Angelaud, R.; Landais, Y. Tetrahedron Lett. 1997, 38, 8841. (162) Ley, S. V.; Sternfeld, F.; Taylor, S. Tetrahedron Lett. 1987, 28, 225. (163) Carless, H. A. J.; Malik, S. S. J. Chem. Soc., Chem. Commun. 1995, 2447- 2448. (164) Haller, J.; Strassner, T.; Houk, K. N. J. Am. Chem. Soc. 1997, 119, 8031-8034. (165) Hodgson, R.; Majid, T.; Nelson, A. J. Chem. Soc., Perkin Trans. 1 2002, 1444 - 1454. (166) Alibes, R.; Bayon, P.; deMarch, P.; Figueredo, M.; Font, J.; Marjanet, G. Org. Lett. 2006, 8, 1617-1620. (167) Rubottom, G. M.; Gruber, J. M.; Juve, H. D.; Charleson, D. Org. Synth. 1990, Coll. Vol 7, 282. (168) Adam, W.; Wirth, T. Acc. Chem. Res. 1999, 32, 703-710. 189
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References<br />
(169) McCormick, J. P.; Tomasik, W.; Johnson, M. W. Tetrahedron Lett. 1981, 22,<br />
607.<br />
(170) Deubel, D. V.; Frenking, G. Acc. Chem. Res. 2003, 36, 645-651.<br />
(171) VanRheenen, V.; Cha, D. Y.; Hartley, W. M. Org. Synth. 1978, 58, 43.<br />
(172) Poli, G. Tetrahedron Lett. 1989, 30, 7385.<br />
(173) Lockwood, S. F.; O'Malley, S.; Watumull, D. G.; Hix, L. M.; Jackson, H.;<br />
Nadolski, G.; (USA): 2005, p 130 pp, Cont -in-part of U S Ser No 629,538.<br />
(174) Bordwell, F. G.; Fried, H. E.; Hughes, D. L.; Lynch, T. Y.; Satish, A. V.;<br />
Whang, Y. E. J. Org. Chem. 1990, 55, 3330-3336.<br />
(175) Olmstead, W. N.; Margolin, Z.; Bordwell, F. G. J. Org. Chem. 1980, 45, 3295-<br />
3299.<br />
(176) Eames, J.; Mitchell, H. J.; Nelson, A.; O'Brien, P.; Warren, S.; Wyatt, P. J.<br />
Chem. Soc., Perkin Trans. 1 1999, 1095-1103.<br />
(177) Luche, J. L. J. Am. Chem. Soc. 1978, 100, 2226-2227.<br />
(178) Gemal, A. L.; Luche, J. L. J. Am. Chem. Soc. 1981, 103, 5454-5459.<br />
(179) Krishnamurthy, S.; Brown, H. C. J. Org. Chem. 1977, 42, 1197-201.<br />
(180) Kumamo<strong>to</strong>, T.; Tabe, N.; Yamaguchi, K.; Yagishita, H.; Iwasa, H.; Ishikawa,<br />
T. Tetrahedron 2001, 57, 2717.<br />
(181) D. J. Dixon, personal communication<br />
(182) Wigfield, D. C. Tetrahedron 1979, 35, 449.<br />
(183) Leo A. Paquette, D. C., Philip L. Fuchs and Gary Molander e-EROS<br />
Encyclopedia of Reagents for Organic Synthesis; John Wiley & Sons, Ltd.,<br />
2006.<br />
(184) Czernecki, S.; Georgoulis, C.; Provelenghiou, C. Tetrahedron Lett. 1976, 17,<br />
3535.<br />
(185) Owensby, D. A.; Parker, A. J.; Diggle, J. W. J. Am. Chem. Soc. 1974, 96, 2682-<br />
2688.<br />
(186) Wessel, H. P.; Iversen, T.; Bundle, D. R. J. Chem. Soc., Perkin Trans. 1 1985,<br />
2247-2250.<br />
(187) Henbest, H. B.; Wilson, R. A. L. J. Chem. Soc. 1957, 1958 - 1965.<br />
(188) Katsuki, T.; Sharpless, K. B. J. Am. Chem. Soc. 1980, 102, 5974-5976.<br />
(189) McKittrick, B. A.; Ganem, B. Tetrahedron Lett. 1985, 26, 4895.<br />
(190) Sharpless, K. B.; Michaelson, R. C. J. Am. Chem. Soc. 1973, 95, 6136-6137.<br />
(191) Cha, J. K.; Christ, W. J.; Kishi, Y. Tetrahedron 1984, 40, 2247.<br />
(192) Cha, J. K.; Kim, N.-S. Chem. Rev. 1995, 95, 1761-1795.<br />
(193) Evans, D. A.; Kaldor, S. W. J. Org. Chem. 1990, 55, 1698-1700.<br />
(194) In Haller & Houk, 1997, the final sentence of the results and discussion reads<br />
"<strong>The</strong> Kishi model is also valid in cyclic alkenes where the stereogenic centre is<br />
fixed in a position resembling that dictated by the 1,3-allylic strain."<br />
(195) Donohoe, T. J.; Garg, R.; Moore, P. R. Tetrahedron Lett. 1996, 37, 3407.<br />
(196) Arjona, O.; de Dios, A.; Plumet, J.; Saez, B. J. Org. Chem. 1995, 60, 4932-<br />
4935.<br />
(197) Pearlman, W. M. Tetrahedron Lett. 1967, 8, 1663.<br />
(198) Jacobsen, E. N.; Marko, I.; France, M. B.; Svendsen, J. S.; Sharpless, K. B. J.<br />
Am. Chem. Soc. 1989, 111, 737-739.<br />
(199) Donohoe, T. J.; Blades, K.; Moore, P. R.; Waring, M. J.; Winter, J. J. G.;<br />
Helliwell, M.; Newcombe, N. J.; Stemp, G. J. Org. Chem. 2002, 67, 7946-<br />
7956.<br />
(200) Fürst, A.; Plattner, P. A. Helv. Chim. Acta 1949, 32, 275-283.<br />
(201) Gonzalez, C.; Carballido, M.; Castedo, L. J. Org. Chem. 2003, 68, 2248-2255.<br />
190