The conjugate addition of enantiomerically pure lithium amides as homochiral ammonia equivalents: Scope, limitations and synthetic applications

Tetrahedron Asymmetry

Volumn 16, Issue 17, 2005, Pages 2833-2891

  Davies, Stephen G ^a   Smith, Andrew D ^a   Price, Paul D ^a  

^a UNIVERSITY OF OXFORD   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

ACRYLIC ACID DERIVATIVE; AMIDE; AMINE; AMMONIA; BETA AMINO ACID; CARBOXYLIC ACID DERIVATIVE; CYCLOPENTENE DERIVATIVE; IRON; LITHIUM; NITROGEN DERIVATIVE;

ADDITION REACTION; ALDOL REACTION; ASYMMETRIC SYNTHESIS; CHIRALITY; CYCLIZATION; DEPROTECTION REACTION; ENANTIOMER; HYDROGENATION; KINETICS; METHODOLOGY; OXIDATION; PRIORITY JOURNAL; REVIEW; SYNTHESIS; THERMODYNAMICS;

EID: 24344501374     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetasy.2005.08.006     Document Type: Review

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198. F. Garro-Helion, A. Merzouk, and G. Guibé J. Org. Chem. 58 1993 6109
199. I. Brackenridge, S.G. Davies, D.R. Fenwick, O. Ichihara, and M.E.C. Polywka Tetrahedron 55 1999 533
200. Davies, S. G.; Fenwick, D. R., unpublished results.
201. S.D. Bull, S.G. Davies, and A.D. Smith J. Chem. Soc., Perkin Trans. 1 2001 2931
202. M.E. Bunnage, S.G. Davies, C.J. Goodwin, and I.A.S. Walters Tetrahedron: Asymmetry 5 1994 35
203. W. Zhu, D. Dong, X. Pu, and D. Ma Org. Lett. 7 2005 705
204. J.M. Langenhan, and S.H. Gellman J. Org. Chem. 68 2003 6440
205. R.L. Jarvest, J.M. Berge, P. Brown, C.S.V. Houge-Frydrych, P.J. O'Hanlon, D.J. McNair, A.J. Pope, and S. Rittenhouse Bioorg. Med. Chem. Lett. 13 2003 1265
206. The high stereocontrol asserted upon protonation of an enolate anti- to an adjacent heteroatom is well documented: H.M.L. Davies, L.M. Hodges, and T.M. Gregg J. Org. Chem. 66 2001 7898
207. H.E. Zimmerman Acc. Chem. Res. 20 1987 263
208. J.E. Mohrig, R.E. Rosenberg, J.W. Apostol, M. Bastienaansen, J.W. Evans, S.J. Franklin, C.D. Frisbie, S.S. Fu, M.L. Hamm, C.B. Hirose, D.A. Hunstad, T.L. James, R.W. King, C.J. Larson, H.A. Latham, D.A. Owen, K.A. Stein, and R. Warnet J. Am. Chem. Soc. 119 1997 479
209. L. Banfi, and G. Guanti Tetrahedron: Asymmetry 10 1999 439
210. S.G. Davies, S.W. Epstein, A.C. Garner, O. Ichihara, and A.D. Smith Tetrahedron: Asymmetry 13 2002 1555
211. S.G. Davies, S.W. Epstein, O. Ichihara, and A.D. Smith Synlett 2001 1599
212. M.E. Bunnage, S.G. Davies, and C.J. Goodwin J. Chem. Soc., Perkin Trans. 1 1993 1375
213. Davies, S. G.; Bunnage, M. E., unpublished results.
214. M.E. Bunnage, A.J. Burke, S.G. Davies, N.L. Millican, R.L. Nicholson, P.M. Roberts, and A.D. Smith Org. Biomol. Chem. 1 2003 3708
215. A.J. Burke, S.G. Davies, and C.J.R. Hedgecock Synlett 10 1996 621
216. Davies, S. G.; Roux, B., unpublished results.
217. N. Asao, T. Uyehara, and Y. Yamamoto Tetrahedron 44 1988 4173
218. N. Asao, T. Uyehara, and Y. Yamamoto Tetrahedron 46 1990 4563
219. N. Asao, N. Tsukada, and Y. Yamamoto J. Chem. Soc., Chem. Commun. 1990 1660
220. K. Voigt, A. Lansky, M. Noltemeyer, and A. De Meijere Liebigs Ann. 1996 899
221. S.G. Davies, D. Diez, S.H. Dominguez, N.M. Garrido, D. Kruchinin, P.D. Price, and A.D. Smith Org. Biomol. Chem. 3 2005 1284
222. J.G. Urones, N.M. Garrido, D. Diez, S.H. Dominguez, and S.G. Davies Tetrahedron: Asymmetry 10 1999 1637
223. N. Asao, T. Shimada, T. Sudo, N. Tsukada, K. Yazawa, Y.S. Gyoung, T. Uyehara, and Y. Yamamoto J. Org. Chem. 62 1997 6274
224. Davies, S. G.; Cooke, J. W. B., unpublished results.
225. Davies, S. G.; Cooke, J. W. B.; Price, P. D., unpublished results.
226. M. Körner, M. Findeisen, and N. Sewald Tetrahedron Lett. 39 1998 3463
227. S.G. Davies, C.J.R. Hedgecock, and J.M. McKenna Tetrahedron: Asymmetry 6 1995 827
228. S.G. Davies, and O. Ichihara Tetrahedron: Asymmetry 7 1996 1919
229. For reviews see: S.G. Davies Aldrichim. Acta 23 1990 31
230. S.G. Davies Pure Appl. Chem. 60 1988 13
231. S.G. Davies, I.M. Dordor-Hedgecock, K.H. Sutton, J.C. Walker, R.H. Jones, and K. Prout Tetrahedron 42 1986 5123
232. S.G. Davies, I.M. Dorder-Hedgecock, K.H. Sutton, and J.C. Walker Tetrahedron Lett. 32 1986 3787
233. for alternative synthetic routes to β-lactams using the iron acyl auxiliary and the reaction with an imine see: K. Broadley, and S.G. Davies Tetrahedron Lett. 25 1984 1743 and
234. L.S. Liebeskind, M.E. Welker, and V. Goedken J. Am. Chem. Soc. 106 1984 441
235. 2COCHCHR] and subsequent decomplexation as a route to β-lactams see: S.G. Davies, N.M. Garrido, P.A. McGee, and J.P. Shilvock J. Chem. Soc., Perkin Trans. 1 1999 3105
236. A. Horeau Tetrahedron 31 1975 1307
237. S.G. Davies, and O. Ichihara J. Chem. Soc., Chem. Commun. 1990 1554
238. S.G. Davies, J. Dupont, R.J.C. Easton, O. Ichihara, J.M. McKenna, A.D. Smith, and J.A.A. de Sousa J. Organomet. Chem. 689 2004 4184
239. For representative examples of secondary structure analysis of β-peptides using 2-amino-cyclopentane carboxylates and related structures see: A.M. Brueckner, P. Chakraborty, S.H. Gellman, and U. Diederichsen Angew. Chem., Int. Ed. 42 2003 4395
240. B.R. Huck, J.D. Fisk, I.A. Guzei, H.A. Carlson, and S.H. Gellman J. Am. Chem. Soc. 125 2003 9035
241. J.M. Langenhan, I.A. Guzei, and S.H. Gellman Angew. Chem., Int. Ed. 42 2003 2402
242. M. Schinnerl, J.K. Murray, J.M. Langenhan, and S.H. Gellman Eur. J. Org. Chem. 4 2003 721
243. M.G. Woll, J.D. Fisk, P.R. LePlae, and S.H. Gellman J. Am. Chem. Soc. 124 2002 12447
244. R.P. Cheng, S.H. Gellman, and W.F. DeGrado Chem. Rev. 101 2001 3219
245. Y.J. Chung, L.A. Christianson, H.E. Stanger, D.R. Powell, and S.H. Gellman J. Am. Chem. Soc. 120 1998 10555
246. S. Bailey, S.G. Davies, A.D. Smith, and J.M. Withey Chem. Commun. 2002 2910
247. For a mini review on the effects of non-linear effects in asymmetric synthesis see: H.B. Kagan Adv. Synth. Catal. 2001 343
248. For manuscripts describing non-linear effects and related topics in kinetic resolution reactions see: D.W. Johnson Jr., and D.A. Singleton J. Am. Chem. Soc. 121 1999 9307
249. R.F. Ismagilov J. Org. Chem. 63 1998 3772
250. S.G. Davies, D. Diez, M.M. El Hammouni, A.C. Garner, N.M. Garrido, M.J.C. Long, R.M. Morrison, A.D. Smith, M.J. Sweet, and J.M. Withey Chem. Commun. 2003 2410
251. S.G. Davies, A.C. Garner, M.J.C. Long, R.M. Morrison, P.M. Roberts, E.D. Savory, A.D. Smith, M.J. Sweet, and J.M. Withey Org. Biomol. Chem. 3 2005 2762
252. For selected examples of parallel kinetic resolution see: E. Vedejs, and X. Chen J. Am. Chem. Soc. 119 1997 2584
253. L.-A. Liao, F. Zhang, O. Dmitrenko, R.D. Bach, and J.M. Fox J. Am. Chem. Soc. 126 2004 4490
254. K. Tanaka, and G.C. Fu J. Am. Chem. Soc. 125 2003 8078
255. E. Vedejs, and E. Rozners J. Am. Chem. Soc. 123 2001 2428
256. J. Dehli, and V. Gotor J. Org. Chem. 67 2002 1716
257. T.M. Pedersen, J.F. Jensen, R.E. Humble, T. Rein, D. Tanner, K. Bodmann, and O. Reiser Org. Lett. 2000 535
258. F. Bertozzi, P. Crotti, F. Macchia, M. Pineschi, and B.L. Feringa Angew. Chem., Int. Ed. 40 2001 930
259. A.G. Al-Sehemi, R.S. Atkinson, and C.K. Meades Chem. Commun. 2001 2684
260. Y. Chen, and L. Deng J. Am. Chem. Soc. 123 2001 11302
261. S.G. Davies, A.C. Garner, M.J.C. Long, A.D. Smith, M.J. Sweet, and J.M. Withey Org. Biomol. Chem. 2004 3355
262. C. Börner, W.A. König, and S. Woodward Tetrahedron Lett. 42 2001 327
263. E. Nicholas, K.C. Russell, and V.J. Hruby J. Org. Chem. 58 1993 766
264. B.-S. Lou, G. Li, F.-D. Lung, and V.J. Hruby J. Org. Chem. 60 1995 5509
265. D.R. Williams, W.S. Kissel, and J.J. Li Tetrahedron Lett. 39 1998 8593
266. S.G. Davies, G.J. Hermann, M.J. Sweet, and A.D. Smith Chem. Commun. 2004 1128
267. J.E. Beddow, S.G. Davies, A.D. Smith, and A.J. Russell Chem. Commun. 2004 2778
268. M.T. Reetz Chem. Rev. 99 1999 1121
269. A. Golebiowski, U. Jacobsson, and J. Jurczak Tetrahedron 43 1987 3063
270. K.E. Rittle, C.F. Homnick, G.S. Ponticello, and B.E. Evans J. Org. Chem. 47 1982 3016
271. H. Ina, and C. Kibayashi J. Org. Chem. 58 1993 52
272. A. Chesney, and I.E. Marko Synth. Commun. 20 1990 3167
273. S.G. Davies, A.D. Smith, and A.R. Cowley Synlett 2004 1957
274. G.W.J. Fleet, A. Karpas, R.A. Dwek, L.E. Fellows, A.S. Tyms, S. Petursson, S.K. Namgoong, N.G. Ramsden, P.W. Smith, J.C. Son, F.X. Wilson, D.R. Witty, G.S. Jacob, and T.W. Rademacher FEBS Lett. 237 1998 128
275. For instance see: N. Asano, R.J. Nash, R.J. Molyneux, G.W.J. Fleet, D.D. Long, S.M. Frederiksen, D.G. Marquess, A.L. Lane, D.J. Watkin, and D.A. Winkler Tetrahedron: Asymmetry 11 2000 1645
276. T. Kahara, Y. Hashimoto, and K. Saigo Tetrahedron 55 1999 6453
277. N. Ma, and D. Ma Tetrahedron: Asymmetry 14 2003 1403
278. G. Kim, S. Jung, E. Lee, and N. Kim J. Org. Chem. 68 2003 5395
279. J.F. Costello, S.G. Davies, and O. Ichihara Tetrahedron: Asymmetry 5 1994 1999
280. K. Rudolf, J.M. Hawkins, R.J. Loncharich, and K.N. Houk J. Org. Chem. 53 1988 3879