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0028880837
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For the synthesis of both enantiomers from a single chiral source via alkylations in the presence of additives, see:
-
For the synthesis of both enantiomers from a single chiral source via alkylations in the presence of additives, see:. Alvarez-Ibarra C., Csákÿ A.G., Maroto R., and Quiroga M.L. J. Org. Chem. 60 (1995) 7934-7940
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34
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0030010210
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Stereochemical reversal has also been observed in the alkylation of enolates derived from (S,S)-pseudoephedrine on changing the alkylating agents:
-
Stereochemical reversal has also been observed in the alkylation of enolates derived from (S,S)-pseudoephedrine on changing the alkylating agents:. Meyers A.G., and McKinstry L. J. Org. Chem. 61 (1996) 2428-2440
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Meyers, A.G.1
McKinstry, L.2
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35
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0034670608
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For reviews on this subject, see:
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For reviews on this subject, see:. Groaning M.D., and Meyers A.I. Tetrahedron 56 (2000) 9843-9872
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Groaning, M.D.1
Meyers, A.I.2
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37
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0032486779
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Papers relevant to this work:
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Papers relevant to this work:. Meyers A.I., Seefeld M.A., Lefker B.A., Blake J.F., and Williard P.G. J. Am. Chem. Soc. 120 (1998) 7429-7438
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Meyers, A.I.1
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Lefker, B.A.3
Blake, J.F.4
Williard, P.G.5
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38
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0842328431
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For the origin of stereochemical reversal in the alkylation of Meyers-type lactam enolate, see:
-
For the origin of stereochemical reversal in the alkylation of Meyers-type lactam enolate, see:. Ikuta Y., and Tomoda S. Org. Lett. 6 (2004) 189-192
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33344476694
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For the preparation of phosphonopropanoamides and their application in the Horner-Wadsworth-Emmons (HWE) reaction, see:
-
For the preparation of phosphonopropanoamides and their application in the Horner-Wadsworth-Emmons (HWE) reaction, see:. Hernández-Fernández E., Fernández-Zertuche M., García-Barradas O., Muñoz-Muñiz O., and Ordóñez M. Synlett (2006) 440-444
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Ordóñez, M.5
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43
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Ordóñez M., Hernández-Fernández E., Montiel-Pérez M., Bautista R., Bustos P., Rojas-Cabrera H., Fernández-Zertuche M., and García-Barradas O. Tetrahedron: Asymmetry 18 (2007) 2427-2436
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Bustos, P.5
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García-Barradas, O.8
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45
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59349100958
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note
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31P NMR at 81 MHz.
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46
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33947721060
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For the preparation of α,α -disubstituted β-ketophosphonates using (S)-α-methylbenzylamine as a chiral auxiliary, see:
-
For the preparation of α,α -disubstituted β-ketophosphonates using (S)-α-methylbenzylamine as a chiral auxiliary, see:. Delarue-Cochin S., Pan J.-J., Dauteloup A., Hendra F., Angoh R.G., Joseph D., Stephens P.J., and Cavé C. Tetrahedron: Asymmetry 18 (2007) 685-691
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Pan, J.-J.2
Dauteloup, A.3
Hendra, F.4
Angoh, R.G.5
Joseph, D.6
Stephens, P.J.7
Cavé, C.8
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47
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59349112389
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note
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When the benzylation of 1a was carried out using LDA (<2.0 equiv) the reaction was not complete.
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48
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59349121584
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Identical results were obtained when LDA (3.0, 3.5 and 4.0 equiv) were used in the benzylation of 1a.
-
Identical results were obtained when LDA (3.0, 3.5 and 4.0 equiv) were used in the benzylation of 1a.
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49
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1642358493
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For effect of LiCl on the selectivity, see:
-
For effect of LiCl on the selectivity, see:. Smitrovich J.H., DiMichele L., Qu C., Boice G.N., Nelson T.D., Huffman M.A., and Murry J. J. Org. Chem. 69 (2004) 1903-1908
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Qu, C.3
Boice, G.N.4
Nelson, T.D.5
Huffman, M.A.6
Murry, J.7
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52
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59349086727
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note
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Diethyl phosphonopropanoamides afforded a better E:Z selectivity than dimethyl phosphonopropanoamides in the HWE reaction, see: Ref. 14b.
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53
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0001681677
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For the influence of the base on the stereoselectivity of alkylation reactions, see:
-
For the influence of the base on the stereoselectivity of alkylation reactions, see:. Kawabata T., Wirth T., Yahiro K., Suzuki H., and Fuji K. J. Am. Chem. Soc. 116 (1994) 10809-10810
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Fuji, K.5
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58
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Manzoni L., Belvisi L., Colombo M., Di Carlo E., Fornia A., and Scolastico C. Tetrahedron Lett. 45 (2004) 6311-6315
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Pizzonero M., Hendra F., Delarue-Cochin S., Huu-Dau M.-E.T., Dumas F., Cavé C., Nour M., and d'Angelo J. Tetrahedron: Asymmetry 16 (2005) 3853-3857
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Dumas, F.5
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Nour, M.7
d'Angelo, J.8
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64
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59349121059
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note
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The silyl ether of enolate derived from 1a could not be isolated, even after several attempts.
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