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b were reported. (a) Rathke, M. W.; Nowak, M. J. Org. Chem. 1985, 50, 2624-2626. (b) Sano, S.; Yokoyama, K.; Fukushima, M.; Yagi, T.; Nagao, Y. J. Chem. Soc., Chem. Commun. 1997, 559-560. Sano, S.; Ando, T.; Yokoyama, K.; Nagao, Y. Synlett 1998, 777-779.
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b were reported. (a) Rathke, M. W.; Nowak, M. J. Org. Chem. 1985, 50, 2624-2626. (b) Sano, S.; Yokoyama, K.; Fukushima, M.; Yagi, T.; Nagao, Y. J. Chem. Soc., Chem. Commun. 1997, 559-560. Sano, S.; Ando, T.; Yokoyama, K.; Nagao, Y. Synlett 1998, 777-779.
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b were reported. (a) Rathke, M. W.; Nowak, M. J. Org. Chem. 1985, 50, 2624-2626. (b) Sano, S.; Yokoyama, K.; Fukushima, M.; Yagi, T.; Nagao, Y. J. Chem. Soc., Chem. Commun. 1997, 559-560. Sano, S.; Ando, T.; Yokoyama, K.; Nagao, Y. Synlett 1998, 777-779.
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Some examples: Evans, D. A.; Ripin, D. H. B.; Halstead, D. P.; Campos, K. R. J. Am. Chem. Soc. 1999, 121, 6816-6826. Bender, J. A.; Arif, A. M.; West, F. G. J. Am. Chem. Soc. 1999, 121, 7443-7444. Evans, D. A.; Barnes, D. M.; Johnson, J. S.; Lectka, T.; Matt, P. v.; Miller, S. J.; Murry, J. A.; Norcross, R. D.; Shaughnessy, E. A.; Campos, K. R. J. Am. Chem. Soc. 1999, 121, 7582-7594. Micalizio, G. C.; Roush, W. R. Tetrahedron Lett. 1999, 40, 3351-3354. Roush, W. R.; Sciotti, R. J. J. Am. Chem. Soc. 1994, 116, 6457-6458. Keck, G. E.; Palani, A.; McHardy, S. F. J. Org. Chem. 1994, 59, 3113-3122. Ley, S. V.; Norman, J.; Pinel, C. Tetrahedron Lett. 1994, 35, 2095-2098.
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Evans, D.A.1
Ripin, D.H.B.2
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Campos, K.R.4
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9
-
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0033581158
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Some examples: Evans, D. A.; Ripin, D. H. B.; Halstead, D. P.; Campos, K. R. J. Am. Chem. Soc. 1999, 121, 6816-6826. Bender, J. A.; Arif, A. M.; West, F. G. J. Am. Chem. Soc. 1999, 121, 7443-7444. Evans, D. A.; Barnes, D. M.; Johnson, J. S.; Lectka, T.; Matt, P. v.; Miller, S. J.; Murry, J. A.; Norcross, R. D.; Shaughnessy, E. A.; Campos, K. R. J. Am. Chem. Soc. 1999, 121, 7582-7594. Micalizio, G. C.; Roush, W. R. Tetrahedron Lett. 1999, 40, 3351-3354. Roush, W. R.; Sciotti, R. J. J. Am. Chem. Soc. 1994, 116, 6457-6458. Keck, G. E.; Palani, A.; McHardy, S. F. J. Org. Chem. 1994, 59, 3113-3122. Ley, S. V.; Norman, J.; Pinel, C. Tetrahedron Lett. 1994, 35, 2095-2098.
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(1999)
J. Am. Chem. Soc.
, vol.121
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Bender, J.A.1
Arif, A.M.2
West, F.G.3
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10
-
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0033603850
-
-
Some examples: Evans, D. A.; Ripin, D. H. B.; Halstead, D. P.; Campos, K. R. J. Am. Chem. Soc. 1999, 121, 6816-6826. Bender, J. A.; Arif, A. M.; West, F. G. J. Am. Chem. Soc. 1999, 121, 7443-7444. Evans, D. A.; Barnes, D. M.; Johnson, J. S.; Lectka, T.; Matt, P. v.; Miller, S. J.; Murry, J. A.; Norcross, R. D.; Shaughnessy, E. A.; Campos, K. R. J. Am. Chem. Soc. 1999, 121, 7582-7594. Micalizio, G. C.; Roush, W. R. Tetrahedron Lett. 1999, 40, 3351-3354. Roush, W. R.; Sciotti, R. J. J. Am. Chem. Soc. 1994, 116, 6457-6458. Keck, G. E.; Palani, A.; McHardy, S. F. J. Org. Chem. 1994, 59, 3113-3122. Ley, S. V.; Norman, J.; Pinel, C. Tetrahedron Lett. 1994, 35, 2095-2098.
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(1999)
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, vol.121
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Evans, D.A.1
Barnes, D.M.2
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Lectka, T.4
Matt, P.V.5
Miller, S.J.6
Murry, J.A.7
Norcross, R.D.8
Shaughnessy, E.A.9
Campos, K.R.10
-
11
-
-
0033597151
-
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Some examples: Evans, D. A.; Ripin, D. H. B.; Halstead, D. P.; Campos, K. R. J. Am. Chem. Soc. 1999, 121, 6816-6826. Bender, J. A.; Arif, A. M.; West, F. G. J. Am. Chem. Soc. 1999, 121, 7443-7444. Evans, D. A.; Barnes, D. M.; Johnson, J. S.; Lectka, T.; Matt, P. v.; Miller, S. J.; Murry, J. A.; Norcross, R. D.; Shaughnessy, E. A.; Campos, K. R. J. Am. Chem. Soc. 1999, 121, 7582-7594. Micalizio, G. C.; Roush, W. R. Tetrahedron Lett. 1999, 40, 3351-3354. Roush, W. R.; Sciotti, R. J. J. Am. Chem. Soc. 1994, 116, 6457-6458. Keck, G. E.; Palani, A.; McHardy, S. F. J. Org. Chem. 1994, 59, 3113-3122. Ley, S. V.; Norman, J.; Pinel, C. Tetrahedron Lett. 1994, 35, 2095-2098.
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(1999)
Tetrahedron Lett.
, vol.40
, pp. 3351-3354
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Micalizio, G.C.1
Roush, W.R.2
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12
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0027939749
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Some examples: Evans, D. A.; Ripin, D. H. B.; Halstead, D. P.; Campos, K. R. J. Am. Chem. Soc. 1999, 121, 6816-6826. Bender, J. A.; Arif, A. M.; West, F. G. J. Am. Chem. Soc. 1999, 121, 7443-7444. Evans, D. A.; Barnes, D. M.; Johnson, J. S.; Lectka, T.; Matt, P. v.; Miller, S. J.; Murry, J. A.; Norcross, R. D.; Shaughnessy, E. A.; Campos, K. R. J. Am. Chem. Soc. 1999, 121, 7582-7594. Micalizio, G. C.; Roush, W. R. Tetrahedron Lett. 1999, 40, 3351-3354. Roush, W. R.; Sciotti, R. J. J. Am. Chem. Soc. 1994, 116, 6457-6458. Keck, G. E.; Palani, A.; McHardy, S. F. J. Org. Chem. 1994, 59, 3113-3122. Ley, S. V.; Norman, J.; Pinel, C. Tetrahedron Lett. 1994, 35, 2095-2098.
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, vol.116
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0001088883
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Some examples: Evans, D. A.; Ripin, D. H. B.; Halstead, D. P.; Campos, K. R. J. Am. Chem. Soc. 1999, 121, 6816-6826. Bender, J. A.; Arif, A. M.; West, F. G. J. Am. Chem. Soc. 1999, 121, 7443-7444. Evans, D. A.; Barnes, D. M.; Johnson, J. S.; Lectka, T.; Matt, P. v.; Miller, S. J.; Murry, J. A.; Norcross, R. D.; Shaughnessy, E. A.; Campos, K. R. J. Am. Chem. Soc. 1999, 121, 7582-7594. Micalizio, G. C.; Roush, W. R. Tetrahedron Lett. 1999, 40, 3351-3354. Roush, W. R.; Sciotti, R. J. J. Am. Chem. Soc. 1994, 116, 6457-6458. Keck, G. E.; Palani, A.; McHardy, S. F. J. Org. Chem. 1994, 59, 3113-3122. Ley, S. V.; Norman, J.; Pinel, C. Tetrahedron Lett. 1994, 35, 2095-2098.
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J. Org. Chem.
, vol.59
, pp. 3113-3122
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Keck, G.E.1
Palani, A.2
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14
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Some examples: Evans, D. A.; Ripin, D. H. B.; Halstead, D. P.; Campos, K. R. J. Am. Chem. Soc. 1999, 121, 6816-6826. Bender, J. A.; Arif, A. M.; West, F. G. J. Am. Chem. Soc. 1999, 121, 7443-7444. Evans, D. A.; Barnes, D. M.; Johnson, J. S.; Lectka, T.; Matt, P. v.; Miller, S. J.; Murry, J. A.; Norcross, R. D.; Shaughnessy, E. A.; Campos, K. R. J. Am. Chem. Soc. 1999, 121, 7582-7594. Micalizio, G. C.; Roush, W. R. Tetrahedron Lett. 1999, 40, 3351-3354. Roush, W. R.; Sciotti, R. J. J. Am. Chem. Soc. 1994, 116, 6457-6458. Keck, G. E.; Palani, A.; McHardy, S. F. J. Org. Chem. 1994, 59, 3113-3122. Ley, S. V.; Norman, J.; Pinel, C. Tetrahedron Lett. 1994, 35, 2095-2098.
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Tetrahedron Lett.
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Now both la and 1b are commercially available from Tokyo Kasei Kogyo Co., Ltd.
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(d) Ando, K. J. Org. Chem. 1999, 64, 8406- 8408. Now both la and 1b are commercially available from Tokyo Kasei Kogyo Co., Ltd.
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Ishii, K.; Ohno, H.; Takemoto, Y.; Ibuka, T. Synlett 1999, 228- 230. Ishii, K.; Ohno, H.; Takemoto, Y.; Osawa, E.; Yamaoka, Y.; Fujii, N.; Ibuka, T. J. Chem. Soc., Perkin Trans. 1 1999, 2155-2163.
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note
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6b the isolation of the product was easier than the original one.
-
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35
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0342688834
-
-
note
-
HMPA was added to the mixture after deprotonation with NaI/ DBU. In the presence of 1 equiv of HMPA, the Z-selectivity of the reaction was not reproducible. We did the reaction four times and got 89%, 90%, 91%, 93% Z-selectivities in 93-94% yields.
-
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36
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and references therein
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For mechanistic studies of the HWE reaction using ab initio calculations; Ando, K. J. Org. Chem. 1999, 64, 6815-6821 and references therein.
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(1999)
J. Org. Chem.
, vol.64
, pp. 6815-6821
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Ando, K.1
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