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0029996546
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A variety of transition-metal-catalyzed propargylic substitution reactions of propargylic alcohol derivatives with heteroatom-centered nucleophiles have been reported: a J. A. Marshall, M. A. Wolf, J. Org. Chem. 1996, 61, 3238;
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A variety of transition-metal-catalyzed propargylic substitution reactions of propargylic alcohol derivatives with heteroatom-centered nucleophiles have been reported: a) J. A. Marshall, M. A. Wolf, J. Org. Chem. 1996, 61, 3238;
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33750167114
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and references therein. For a recent review, see
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For a recent review, see: L. Zani, C. Bolm, Chem. Commun. 2006, 4263, and references therein.
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For examples, see: a) C. Wei, C.-J. Li, J. Am. Chem. Soc. 2002, 124, 5638;
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a) R. J. Detz, M. M. E. Delville, H. Hiemstra, J. H. van Maarseveen, Angew. Chem. 2008, 120, 3837;
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37
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53549114563
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Maarseveen and his co-workers
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presented, June 15, Amsterdam
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b) Prof. Maarseveen and his co-workers presented a part of the result at the PAC-Symposium 2007 (June 15, 2007, Amsterdam).
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(2007)
a part of the result at the PAC-Symposium
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Prof1
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38
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53549126412
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Binap, 2,2′-bis(diphenylphosphino)-1,1′-binaphthyl
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Binap = 2,2′-bis(diphenylphosphino)-1,1′-binaphthyl.
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53549120018
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Biphep, 2,2′-bis(diphenylphosphino)-1,1′-biphenyl
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Biphep = 2,2′-bis(diphenylphosphino)-1,1′-biphenyl.
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40
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53549126701
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No reaction occurred in the absence of N,N-diisopropylethylamine. When triethylamine was used in place of N,N-diisopropylethylamine as a base, a similar enantioselectivity was observed.
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No reaction occurred in the absence of N,N-diisopropylethylamine. When triethylamine was used in place of N,N-diisopropylethylamine as a base, a similar enantioselectivity was observed.
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41
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53549109218
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(R)-Cl-MeO-biphep=(R)-5,5′-dichloro-6, 6′-dimethoxy-2,2′-bis(diphenylphosphino)-1,1′-biphenyl, is a commercially available reagent from Strem Chemicals.
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(R)-Cl-MeO-biphep=(R)-5,5′-dichloro-6, 6′-dimethoxy-2,2′-bis(diphenylphosphino)-1,1′-biphenyl, is a commercially available reagent from Strem Chemicals.
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0141534442
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a) R. R. Huddleston, H.-Y. Jang, M. J. Krische, J. Am. Chem. Soc. 2003, 125, 11488;
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Huddleston, R.R.1
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b) H.-Y. Jang, F. W. Hughes, H. Gong, J. Zhang, J. S. Brodbelt, M. J. Krische, J. Am. Chem. Soc. 2005, 127, 6174;
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Jang, H.-Y.1
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Krische, M.J.6
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45
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53549100257
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2, toluene, THF, MeCN, DMF, and 1,4-dioxane.
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2, toluene, THF, MeCN, DMF, and 1,4-dioxane.
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53549097720
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Although a variety of optically active diphosphines and monophosphines, such as Duphos, chiraphos, diop, and mop, were investigated as chiral ligands for the propargylic amination, these did not work effectively. As a result, R-Cl-MeO-biphep was found to be the ligand of choice for the present propargylic amination. The detailed experimental results will be reported in due course
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Although a variety of optically active diphosphines and monophosphines, such as Duphos, chiraphos, diop, and mop, were investigated as chiral ligands for the propargylic amination, these did not work effectively. As a result, (R)-Cl-MeO-biphep was found to be the ligand of choice for the present propargylic amination. The detailed experimental results will be reported in due course.
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D. Pei, Z. Wang, S. Wei, Y. Zhang, J. Sun, Org. Lett. 2006, 8, 5913.
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Org. Lett
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Pei, D.1
Wang, Z.2
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A. M. Johns, N. Sakai, A. Ridder, J. F. Hartwig, J. Am. Chem. Soc. 2006, 128, 9306.
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J. Am. Chem. Soc
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Johns, A.M.1
Sakai, N.2
Ridder, A.3
Hartwig, J.F.4
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49
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The molecular structure of a copper-(R)-Cl-MeO-biphep complex has been determined by X-ray crystallography. The detailed experimental results will be reported in due course.
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The molecular structure of a copper-(R)-Cl-MeO-biphep complex has been determined by X-ray crystallography. The detailed experimental results will be reported in due course.
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50
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Y. Nishibayashi, M. D. Milton, Y. Inada, M. Yoshikawa, I. Wakiji, M. Hidai, S. Uemura, Chem. Eur. J. 2005, 11, 1433.
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Nishibayashi, Y.1
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Inada, Y.3
Yoshikawa, M.4
Wakiji, I.5
Hidai, M.6
Uemura, S.7
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