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Zhu. J.; Price, B. A.; Zhao, S. X.; Skonezny, P. M. Tetrahedron Lett. 2000, 41, 4011.
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Zhu, J.1
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(b) Denney, D. B.; Vill, J. J.; Boskin, M. J. J. Am. Chem. Soc. 1962, 84, 3944.
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Denney, D.B.1
Vill, J.J.2
Boskin, M.J.3
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0000968627
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and references therein
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(c) Jacks, T. E.; Nibbe, H.; Wiemer, D. F. J. Org. Chem. 1993, 58, 4584 and references therein.
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Jacks, T.E.1
Nibbe, H.2
Wiemer, D.F.3
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Gadamasetti K., Ed.; Dekker: New York
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c however, these methods were not suitable for scale-up: (a) Senanayake, C. H.; Jacobsen, E. N. In Process Chemistry in the Pharmaceutical Industry; Gadamasetti, K., Ed.; Dekker: New York, 1999; p 347. (b) Palucki, M.; Pospisil, P. J.; Zhang, W.; Jacobsen, E. N. J. Am. Chem. Soc. 1994, 20, 9333. (c) Goswami, A.; Totleben, M. J.; Singh, A. K.; Patel, R. N. Tetrahedron: Asymmetry 1999, 3167. (c) Goswami, A.; Totleben, M. J.; Singh, A. K.; Patel, R. N. Tetrahedron: Asymmetry 1999, 3167.
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Process Chemistry in the Pharmaceutical Industry
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Senanayake, C.H.1
Jacobsen, E.N.2
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11
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0001580728
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c however, these methods were not suitable for scale-up: (a) Senanayake, C. H.; Jacobsen, E. N. In Process Chemistry in the Pharmaceutical Industry; Gadamasetti, K., Ed.; Dekker: New York, 1999; p 347. (b) Palucki, M.; Pospisil, P. J.; Zhang, W.; Jacobsen, E. N. J. Am. Chem. Soc. 1994, 20, 9333. (c) Goswami, A.; Totleben, M. J.; Singh, A. K.; Patel, R. N. Tetrahedron: Asymmetry 1999, 3167. (c) Goswami, A.; Totleben, M. J.; Singh, A. K.; Patel, R. N. Tetrahedron: Asymmetry 1999, 3167.
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J. Am. Chem. Soc.
, vol.20
, pp. 9333
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Palucki, M.1
Pospisil, P.J.2
Zhang, W.3
Jacobsen, E.N.4
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12
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0033551906
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c however, these methods were not suitable for scale-up: (a) Senanayake, C. H.; Jacobsen, E. N. In Process Chemistry in the Pharmaceutical Industry; Gadamasetti, K., Ed.; Dekker: New York, 1999; p 347. (b) Palucki, M.; Pospisil, P. J.; Zhang, W.; Jacobsen, E. N. J. Am. Chem. Soc. 1994, 20, 9333. (c) Goswami, A.; Totleben, M. J.; Singh, A. K.; Patel, R. N. Tetrahedron: Asymmetry 1999, 3167. (c) Goswami, A.; Totleben, M. J.; Singh, A. K.; Patel, R. N. Tetrahedron: Asymmetry 1999, 3167.
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(1999)
Tetrahedron: Asymmetry
, pp. 3167
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Goswami, A.1
Totleben, M.J.2
Singh, A.K.3
Patel, R.N.4
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14
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4444276636
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(b) Kolb, H. C.; VanNieuwenhze, M. S.; Sharpless, K. B. Chem. Rev. 1994, 94, 2483.
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Kolb, H.C.1
VanNieuwenhze, M.S.2
Sharpless, K.B.3
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15
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0141712450
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(c) Sharpless, K. B.; Amberg, W.; Bennani, Y. L.; Crispino, G. A.; Hartung, J.; Jeong, K.-S.; Kwong, H.-L.; Morikawa, K.; Wang, Z.-M.; Xu, D.; Zhang, X.-L. J. Org. Chem. 1992, 57, 2768.
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Sharpless, K.B.1
Amberg, W.2
Bennani, Y.L.3
Crispino, G.A.4
Hartung, J.5
Jeong, K.-S.6
Kwong, H.-L.7
Morikawa, K.8
Wang, Z.-M.9
Xu, D.10
Zhang, X.-L.11
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17
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0010852484
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note
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There was no product formation with triethylamine or diisopropylethylamine (DIPEA) in THF at 65°C. About 16% product formed using DIPEA in combination with 1 equiv of LiBr and DIPEA as the reaction solvent at 100 °C.
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18
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0010844727
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note
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Although DME is a common solvent, appropriate protective measures must be taken when handling DME due to possible teratogenic (target organ: liver, kidneys) and reproductive hazard effects.
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19
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0010776446
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note
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A peroxide inhibitor (BHT) was added to the DME distillate.
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