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1
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32644439884
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For recent reviews on the generation of quaternary stereocenters, see: a
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For recent reviews on the generation of quaternary stereocenters, see: a) B. M. Trost, C. Jiang, Synthesis 2006, 369-396;
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0042969710
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Ed, J. D. Morrison, Academic Press, New York, chap. 1
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D. A. Evans in Asymmetric Synthesis, Vol. 3 (Ed.: J. D. Morrison), Academic Press, New York, 1984, chap. 1.
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Evans, D.A.1
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For α-allylation of enolates, see: a, Ed, I. Ojima, VCH Publishers, New York
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For α-allylation of enolates, see: a) T. Hayashi in Catalytic Asymmetric Synthesis (Ed.: I. Ojima), VCH Publishers, New York, 1993;
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Catalytic Asymmetric Synthesis
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Hayashi, T.1
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for α-arylation of enolates, see: e
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for α-arylation of enolates, see: e) J. Åhman, J. P. Wolfe, M. V. Troutman, M. Palucki, S. L. Buchwald, J. Am. Chem. Soc. 1998, 120, 1918-1919;
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0035859320
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for α-vinylation of enolates, see: g
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for α-vinylation of enolates, see: g) A. Chieffi, K. Kamikawa, J. Åhman, J. M. Fox, S. L. Buchwald, Org. Lett. 2001, 3, 1897-1900.
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33845470711
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For the α-alkylation reaction of enolates, see: a
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For the α-alkylation reaction of enolates, see: a) U.-H. Dolling, P. Davis, E. J. Grabowski, J. Am. Chem. Soc. 1984, 106, 446-447;
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For conjugate addition reactions of enolates, see: a
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For conjugate addition reactions of enolates, see: a) J. Christoffers, A. Baro, Angew. Chem. 2003, 115, 1726-1728;
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Angew. Chem. Int. Ed. 2003, 42, 1688-1690, and references therein;
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c) H. Sasai, E. Emori, T. Arai, M. Shibasaki, Tetrahedron Lett. 1996, 37, 5561-5564;
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h) T. Ooi, T. Miki, M. Taniguchi, M. Shiraishi, M. Takeuchi, K. Maruoka, Angew. Chem. 2003, 115, 3926-3928;
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Angew. Chem. Int. Ed. 2003, 42, 3796-3798;
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j) F. Wu, H. Li, R. Hong, L. Deng, Angew. Chem. 2006, 118, 961-964;
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11844302258
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For additions of enolates to nitroolefins, see: a
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For additions of enolates to nitroolefins, see: a) T. Okino, Y. Hoashi, T. Furukawa, X. Xu, Y. Takemoto, J. Am. Chem. Soc. 2005, 127, 119-125;
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b) H. Li, Y. Wang, L. Tang, F. Wu, X. Liu, C. Guo, B. M. Foxman, L. Deng, Angew. Chem. 2005, 117, 107-110;
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Li, H.1
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33845922590
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Angew. Chem. Int. Ed. 2005, 44, 105-108;
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Chem. Int. Ed
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Angew1
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34
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33744823336
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for additions of enolates to vinyl sulfones, see: c
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for additions of enolates to vinyl sulfones, see: c) T.-Y. Liu, J. Long, B.-J. Li, L. Jiang, R. Li, Y. Wu, L.-S. Ding, Y.-C. Chen, Org. Biomol. Chem. 2006, 4, 2097-2099.
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Chen, Y.-C.8
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35
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0037427250
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For acylation reactions of enolates, see: a
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For acylation reactions of enolates, see: a) A. H. Mermerian, G. C. Fu, J. Am. Chem. Soc. 2003, 125, 4050-4051.
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Mermerian, A.H.1
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33744733390
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For Mannich reactions, see: a A. Ting, S. Lou, S. E. Schaus, Org. Lett. 2006, 8, 2003-2006, and references therein;
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For Mannich reactions, see: a) A. Ting, S. Lou, S. E. Schaus, Org. Lett. 2006, 8, 2003-2006, and references therein;
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37
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0037495950
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b) M. Marigo, A. Kjærsgaard, K. Juhl, N. Gathergood, K. A. Jørgensen, Chem. Eur. J. 2003, 9, 2359-2367;
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Marigo, M.1
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Gathergood, N.4
Jørgensen, K.A.5
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38
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4644286223
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for aldol additions, see: c
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for aldol additions, see: c) S. Ishikawa, T. Hamada, K. Manabe, S. Kobayashi, J. Am. Chem. Soc. 2004, 126, 12 236-12 237.
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Ishikawa, S.1
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39
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0010683114
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For the synthesis of tetrasubstituted tributyltin ketone enolates, see: a
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For the synthesis of tetrasubstituted tributyltin ketone enolates, see: a) F. Guibéz, Y. T. Xian, A. N. Zigna, G. Balavoine, Tetrahedron Lett. 1985, 26, 3559-3562;
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Guibéz, F.1
Xian, Y.T.2
Zigna, A.N.3
Balavoine, G.4
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40
-
-
0001617788
-
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for the synthesis of tetrasubstituted silyl enol ethers from ketenes, see: b
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for the synthesis of tetrasubstituted silyl enol ethers from ketenes, see: b) R. Häner, T. Laube, D. Seebach, J. Am. Chem. Soc. 1985, 107, 5396-5403;
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Häner, R.1
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Seebach, D.3
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41
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0001153549
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for purification by distillation using a spinning-band column, see: c
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for purification by distillation using a spinning-band column, see: c) S. Yamago, D. Machii, E. Nakamura, J. Org. Chem. 1991, 56, 2098-2106.
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Yamago, S.1
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42
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0000291898
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For successful diastereoselective examples, see: a
-
For successful diastereoselective examples, see: a) D. Enders, A. Zamponi, T. Schäfer, C. Nübling, H. Eichenauer, A. S. Demir, G. Raabe, Chem. Ber. 1994, 127, 1707-1721;
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d) T. Abe, T. Suzuki, K. Sekiguchi, S. Hosokawa, S. Kobayshi, Tetrahedron Lett. 2003, 44, 9303-9305;
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e) A. Arpin, J. M. Manthorpe, J. L. Gleason, Org. Lett. 2006, 8, 1359-1362, and references therein;
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47
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17644423068
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for a successful catalytic example, see: f
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for a successful catalytic example, see: f) A. H. Mermerian, G. C. Fu, J. Am. Chem. Soc. 2005, 127, 5604-5607.
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50
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34250839206
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-
See the Supporting Information for details
-
See the Supporting Information for details.
-
-
-
-
51
-
-
34250840969
-
-
The para-siloxy salen ligands were prepared in three steps and in high overall yield (70-80%) from the commercially available tert- butylhydroquinone; see the Supporting Information for details.
-
The para-siloxy salen ligands were prepared in three steps and in high overall yield (70-80%) from the commercially available tert- butylhydroquinone; see the Supporting Information for details.
-
-
-
-
52
-
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34250826312
-
-
Treatment of the [(salen)CrCl] complex 1b with NaI at room temperature resulted in the quantitative exchange of the counterion; see the Supporting Information for details
-
Treatment of the [(salen)CrCl] complex 1b with NaI at room temperature resulted in the quantitative exchange of the counterion; see the Supporting Information for details
-
-
-
-
53
-
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0012008854
-
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The absolute configuration of 4a was assigned by hydrogenation to 2-ethyl-2-methylpentanoic acid and by comparison of its optical rotation to literature values, see reference [10f] and also: a W. v. E. Doering, K. B. Wiberg, J. Am. Chem. Soc. 1950, 72, 2608-2610;
-
The absolute configuration of 4a was assigned by hydrogenation to 2-ethyl-2-methylpentanoic acid and by comparison of its optical rotation to literature values, see reference [10f] and also: a) W. v. E. Doering, K. B. Wiberg, J. Am. Chem. Soc. 1950, 72, 2608-2610;
-
-
-
-
55
-
-
0011955265
-
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The absolute configurations of products 3 were inferred from this assignment
-
c) F. S. Prout, B. Burachinsky, W. T. Brannen, H. L. Young, J. Org. Chem. 1960, 25, 835-838. The absolute configurations of products 3 were inferred from this assignment.
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J. Org. Chem
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Prout, F.S.1
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34250825732
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For state-of-the-art preparations of 4a and 4b, see: a H. Leuser, S. Perrone, F. Liron, F. F. Kneisel, P. Knochel, Angew. Chem. 2005, 117, 4703-4707;
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For state-of-the-art preparations of 4a and 4b, see: a) H. Leuser, S. Perrone, F. Liron, F. F. Kneisel, P. Knochel, Angew. Chem. 2005, 117, 4703-4707;
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57
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22744434029
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Angew. Chem. Int. Ed. 2005, 44, 4627-4631, and references therein;
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Angew. Chem. Int. Ed. 2005, 44, 4627-4631, and references therein;
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58
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16844367372
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also see: b J. Wu, D. M. Mampreian, A. H. Hoveyda, J. Am. Chem. Soc. 2005, 127, 4584-4585;
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also see: b) J. Wu, D. M. Mampreian, A. H. Hoveyda, J. Am. Chem. Soc. 2005, 127, 4584-4585;
-
-
-
-
60
-
-
34250842983
-
-
13C NMR spectroscopy have been inconclusive.
-
13C NMR spectroscopy have been inconclusive.
-
-
-
-
61
-
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33845556160
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For observations of reactions of E and Z enolates that react with 2- to 8-fold differences in rate, see: a D. A. Evans, J. V. Nelson, E. Vogel, T. R. Taber, J. Am. Chem. Soc. 1981, 103, 3099-3111;
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For observations of reactions of E and Z enolates that react with 2- to 8-fold differences in rate, see: a) D. A. Evans, J. V. Nelson, E. Vogel, T. R. Taber, J. Am. Chem. Soc. 1981, 103, 3099-3111;
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62
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0002477225
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J. E. Dubois, P. Felmann, Tetrahedron Lett. 1975, 16, 1225-1228. Assuming that the isomeric mixture of the tin enolates undergo alkylation with identical enantioselectivity, a maximum 9-fold difference in rate is necessary to explain the observed levels of enantioselectivity for the alkylation of a 1.5:1 mixture of E/Z tin enolates.
-
b) J. E. Dubois, P. Felmann, Tetrahedron Lett. 1975, 16, 1225-1228. Assuming that the isomeric mixture of the tin enolates undergo alkylation with identical enantioselectivity, a maximum 9-fold difference in rate is necessary to explain the observed levels of enantioselectivity for the alkylation of a 1.5:1 mixture of E/Z tin enolates.
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-
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