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2Si protection with an aminosilane: Liepin'sh, E. E.; Birgele, I. S.; Zelchan, G. I.; Urtane, I. P.; Lukevits, E. J. Gen. Chem. USSR (Engl. Transl.) 1980, 50, 2212-2216.
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Liepin'sh, E.E.1
Birgele, I.S.2
Zelchan, G.I.3
Urtane, I.P.4
Lukevits, E.5
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86
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48249138908
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2Si protection with an aminosilane: reference 24g.
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2Si protection with an aminosilane: reference 24g.
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-
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87
-
-
85005706466
-
-
and references cited therein
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(a) Chan, T. H.; Fleming, I. Synthesis 1979, 761-786, and references cited therein.
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(1979)
Synthesis
, pp. 761-786
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Chan, T.H.1
Fleming, I.2
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89
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48249114267
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TiCl4, SnCl4, ZrCl4, MgBr 2·OEt2, Cu(OTf)2, BF3· OEt2, Yb(OTf)3, MeAlCl2, Me3SiOTf, t-BuMe2SiOTf, Me3SiOTf/DTBMP, and TfOH were investigated
-
3SiOTf/DTBMP, and TfOH were investigated.
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91
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0035122651
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Crich, D.; Smith, M.; Yao, Q.; Picione, J. Synthesis 2001, 323-326.
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Synthesis
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Crich, D.1
Smith, M.2
Yao, Q.3
Picione, J.4
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92
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48249092538
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The silyl ether tether decomposed rapidly in the presence of TfOH
-
The silyl ether tether decomposed rapidly in the presence of TfOH.
-
-
-
-
93
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48249123007
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4 at -78°C for 24 h. The lack of product formation in this reaction, combined with the generation of the desired oxasilacycles when tethered allylsilanes containing bulkier groups at the silyl ether connection were employed, confirms that the mechanism of diene formation involves an intramolecular allylation step.
-
4 at -78°C for 24 h. The lack of product formation in this reaction, combined with the generation of the desired oxasilacycles when tethered allylsilanes containing bulkier groups at the silyl ether connection were employed, confirms that the mechanism of diene formation involves an intramolecular allylation step.
-
-
-
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94
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59849087060
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Product Subclass 37: β-Silyl Alcohols and the Peterson Reaction
-
Fleming, I, Ed, Georg Thieme Verlag: Stuttgart, Germany, Chapter 4.4.37, pp
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(a) Ager, D. J. Product Subclass 37: β-Silyl Alcohols and the Peterson Reaction. In Science of Synthesis; Fleming, I., Ed.; Georg Thieme Verlag: Stuttgart, Germany, 2002; Vol. 4, Chapter 4.4.37, pp 789-809.
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Science of Synthesis
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Ager, D.J.1
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0002974335
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(b) Ager, D. J. Org. React. 1990, 38, 1-223.
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Org. React
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Ager, D.J.1
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98
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37049096935
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Evidence for a stepwise reaction mechanism in the reaction of allylsilanes with electrophiles: Fleming, I.; Langley, J. A. J. Chem. Soc., Perkin Trans. 1 1981, 1421-1423.
-
Evidence for a stepwise reaction mechanism in the reaction of allylsilanes with electrophiles: Fleming, I.; Langley, J. A. J. Chem. Soc., Perkin Trans. 1 1981, 1421-1423.
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-
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99
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0032900270
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Lambert, J. B.; Zhao, Y.; Emblidge, R. W.; Salvador, L. A.; Liu, X. Y.; So, J. H.; Chelius, E. C. Acc. Chem. Res. 1999, 32, 183-190.
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Acc. Chem. Res
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Lambert, J.B.1
Zhao, Y.2
Emblidge, R.W.3
Salvador, L.A.4
Liu, X.Y.5
So, J.H.6
Chelius, E.C.7
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100
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48249120229
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-
The energetic barrier to bond rotation will be very low
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The energetic barrier to bond rotation will be very low.
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-
-
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101
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33644751690
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(a) Merten, J.; Hennig, A.; Schwab, P.; Fröhlich, R.; Tokalov, S. V.; Gutzeit, H. O.; Metz, P. Eur. J. Org. Chem. 2006, 1144-1161.
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Eur. J. Org. Chem
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Merten, J.1
Hennig, A.2
Schwab, P.3
Fröhlich, R.4
Tokalov, S.V.5
Gutzeit, H.O.6
Metz, P.7
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102
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0037006835
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(b) Alcaide, B.; Almendros, P.; Aragoncillo, C. Chem. Eur. J. 2002, 8, 1719-1729.
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Chem. Eur. J
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Alcaide, B.1
Almendros, P.2
Aragoncillo, C.3
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106
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0010402967
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(f) Angell, R.; Parsons, P. J.; Naylor, A.; Tyrrell, E. Synlett 1992, 599-600.
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(1992)
Synlett
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Angell, R.1
Parsons, P.J.2
Naylor, A.3
Tyrrell, E.4
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107
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0028969296
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(g) Suzuki, K.; Hasegawa, T.; Imai, T.; Maeta, H.; Ohba, S. Tetrahedron 1995, 51, 4483-4494.
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(1995)
Tetrahedron
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Suzuki, K.1
Hasegawa, T.2
Imai, T.3
Maeta, H.4
Ohba, S.5
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109
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48249156047
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In our work on the synthesis of β-allyl-C-mannosyl derivatives using a related intramolecular allylation strategy, the isolation of intermediates along this mechanistic pathway supports this proposed mechanism: see reference 23e
-
In our work on the synthesis of β-allyl-C-mannosyl derivatives using a related intramolecular allylation strategy, the isolation of intermediates along this mechanistic pathway supports this proposed mechanism: see reference 23e.
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-
-
-
111
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48249110178
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-
We do not discount a non-concerted elimination pathway in which ionization first generates an allyl carbocationic intermediate, which then collapses to the diene through loss of the trimethylsilyl group. However, the carbocationic intermediate would again be expected to give rise to an (E)-diene product for similar reasons to those outlined in the text
-
We do not discount a non-concerted elimination pathway in which ionization first generates an allyl carbocationic intermediate, which then collapses to the diene through loss of the trimethylsilyl group. However, the carbocationic intermediate would again be expected to give rise to an (E)-diene product for similar reasons to those outlined in the text.
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-
-
-
112
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37049086105
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Zechel, D. L.; Foucher, D. A.; Pudelski, J. K.; Yap, G. P. A.; Rheingold, A. L.; Manners, I. J. Chem. Soc., Dalton Trans. 1995, 1893-1899.
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J. Chem. Soc., Dalton Trans
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-
Zechel, D.L.1
Foucher, D.A.2
Pudelski, J.K.3
Yap, G.P.A.4
Rheingold, A.L.5
Manners, I.6
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113
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48249112429
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This Lewis acid had shown greatest promise in our early studies with 9aa
-
This Lewis acid had shown greatest promise in our early studies with 9aa.
-
-
-
-
114
-
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48249106099
-
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3 substituent, undergo elimination and provide the source of diene; however, the exclusive formation of the (E)-diene would point against this.
-
3 substituent, undergo elimination and provide the source of diene; however, the exclusive formation of the (E)-diene would point against this.
-
-
-
-
115
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48249143460
-
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Diene (E)-27 was not particularly stable; however, in some cases, small amounts of this side product could be isolated by HPLC and at least partially characterized (see the Supporting Information).
-
Diene (E)-27 was not particularly stable; however, in some cases, small amounts of this side product could be isolated by HPLC and at least partially characterized (see the Supporting Information).
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-
-
-
117
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0000485694
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(a) Tamao, K.; Ishida, N.; Kumada, M. J. Org. Chem. 1983, 48, 2120-2122.
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(1983)
J. Org. Chem
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, pp. 2120-2122
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Tamao, K.1
Ishida, N.2
Kumada, M.3
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119
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0000497149
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Tamao, K.; Kakui, T.; Akita, M.; Iwahara, T.; Kanatani, R.; Yoshida, J.; Kumada, M. Tetrahedron 1983, 39, 983-990.
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(1983)
Tetrahedron
, vol.39
, pp. 983-990
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Tamao, K.1
Kakui, T.2
Akita, M.3
Iwahara, T.4
Kanatani, R.5
Yoshida, J.6
Kumada, M.7
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120
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0035842170
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For related approaches see: a
-
For related approaches see: (a) Toshima, K.; Arita, T.; Kato, K.; Tanaka, D.; Matsumura, S. Tetrahedron Lett. 2001, 42, 8873-8876.
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(2001)
Tetrahedron Lett
, vol.42
, pp. 8873-8876
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Toshima, K.1
Arita, T.2
Kato, K.3
Tanaka, D.4
Matsumura, S.5
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121
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0032500142
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(b) Dankwardt, J. W.; Dankwardt, S. M.; Schlessinger, R. H. Tetrahedron Lett. 1998, 39, 4979-4982.
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(1998)
Tetrahedron Lett
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, pp. 4979-4982
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Dankwardt, J.W.1
Dankwardt, S.M.2
Schlessinger, R.H.3
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122
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0030690109
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(c) Shimura, T.; Komatsu, C.; Matsumura, M.; Shimada, Y.; Ohta, K.; Mitsunobu, O. Tetrahedron Lett. 1997, 38, 8341-8344.
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(1997)
Tetrahedron Lett
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, pp. 8341-8344
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Shimura, T.1
Komatsu, C.2
Matsumura, M.3
Shimada, Y.4
Ohta, K.5
Mitsunobu, O.6
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125
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0024537522
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(f) Keck, G. E.; Boden, E. P.; Wiley, M. R. J. Org. Chem. 1989, 54, 896-906.
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J. Org. Chem
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Keck, G.E.1
Boden, E.P.2
Wiley, M.R.3
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126
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48249135348
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Analytically pure samples of the allylation products were obtained by HPLC see the Supporting Information
-
Analytically pure samples of the allylation products were obtained by HPLC (see the Supporting Information).
-
-
-
-
127
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37049069933
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(a) Kocienski, P. J.; Yeates, C.; Street, S. D. A.; Campbell, S. F. J. Chem. Soc., Perkin Trans. 1 1987, 2183-2187.
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Kocienski, P.J.1
Yeates, C.2
Street, S.D.A.3
Campbell, S.F.4
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129
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33751385878
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Rychnovsky, S. D.; Rogers, B.; Yang, G. J. Org. Chem. 1993, 58, 3511-3515.
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J. Org. Chem
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Rychnovsky, S.D.1
Rogers, B.2
Yang, G.3
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131
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0000234052
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Hayashi, T.; Kabeta, K.; Hamachi, I.; Kumada, M. Tetrahedron Lett. 1983, 24, 2865-2868.
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(1983)
Tetrahedron Lett
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, pp. 2865-2868
-
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Hayashi, T.1
Kabeta, K.2
Hamachi, I.3
Kumada, M.4
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132
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33751158182
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Keck, G. E.; Savin, K. A.; Cressman, E. N. K.; Abbott, D. E. J. Org. Chem. 1994, 59, 7889-7896,
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Keck, G.E.1
Savin, K.A.2
Cressman, E.N.K.3
Abbott, D.E.4
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133
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0027530713
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Gevorgyan, V.; Kadota, I.; Yamamoto, Y. Tetrahedron Lett. 1993, 34, 1313-1316.
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Tetrahedron Lett
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, pp. 1313-1316
-
-
Gevorgyan, V.1
Kadota, I.2
Yamamoto, Y.3
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134
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48249100725
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The effect of size of the activator on the stereoselectivity of reactions between aldehydes and allylsilanes has also been observed by Denmark, see references 5b and 5c
-
The effect of size of the activator on the stereoselectivity of reactions between aldehydes and allylsilanes has also been observed by Denmark, see references 5b and 5c.
-
-
-
-
135
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48249113193
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Frontier orbital-controlled allylations have also been proposed by Denmark, see reference 25c.
-
Frontier orbital-controlled allylations have also been proposed by Denmark, see reference 25c.
-
-
-
-
136
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15844376790
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(a) Evans, D. A.; Dart, M. J.; Duffy, J. L.; Yang, M. G. J. Am. Chem. Soc. 1996, 118, 4322-4343.
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J. Am. Chem. Soc
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Evans, D.A.1
Dart, M.J.2
Duffy, J.L.3
Yang, M.G.4
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137
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0027984321
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(b) Evans, D. A.; Duffy, J. L.; Dart, M. J. Tetrahedron Lett. 1994, 35, 8537-8540.
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Tetrahedron Lett
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Evans, D.A.1
Duffy, J.L.2
Dart, M.J.3
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138
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0028034164
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(c) Evans, D. A.; Dart, M. J.; Duffy, J. L. Tetrahedron Lett. 1994, 35, 8541-8544.
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(1994)
Tetrahedron Lett
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Evans, D.A.1
Dart, M.J.2
Duffy, J.L.3
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139
-
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0030851176
-
-
This model has also been supported by computational calculations: Bonini, C, Esposito, V, D'Auria, M, Righi, G. Tetrahedron 1997, 53, 13419-13426
-
This model has also been supported by computational calculations: Bonini, C.; Esposito, V.; D'Auria, M.; Righi, G. Tetrahedron 1997, 53, 13419-13426.
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-
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142
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33750079882
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Jervis, P. J.; Kariuki, B. M.; Cox, L. R. Org. Lett. 2006, 8, 4649-4652.
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Jervis, P.J.1
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Cox, L.R.3
-
143
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0035823879
-
-
Certain aluminum Lewis acids have been proposed to form chelates between carbonyl groups and a β-silyl ether functionality: Evans, D. A, Allison, B. D, Yang, M. G, Masse, C. E. J. Am. Chem. Soc. 2001, 123, 10840-10852
-
Certain aluminum Lewis acids have been proposed to form chelates between carbonyl groups and a β-silyl ether functionality: Evans, D. A.; Allison, B. D.; Yang, M. G.; Masse, C. E. J. Am. Chem. Soc. 2001, 123, 10840-10852.
-
-
-
-
145
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0003536850
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Baldwin, J. E, Ed, Pergamon: Oxford, UK, Chapter 6
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(b) Deslongchamps, P. In Stereoelectronic Effects in Organic Chemistry; Baldwin, J. E., Ed.; Pergamon: Oxford, UK, 1983; Vol. 1, Chapter 6.
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Stereoelectronic Effects in Organic Chemistry
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-
-
Deslongchamps, P.1
-
146
-
-
48249083658
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-
A chelation-control argument cannot be used to rationalize the stereochemical outcome in this example
-
A chelation-control argument cannot be used to rationalize the stereochemical outcome in this example.
-
-
-
|