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For P-chiral phosphorus ligands used in asymmetric hydrogenation, see: ref. [2], p. 3037 and references cited therein; and a) F. Maienza, F. Spindler, M. Thommen, B. Pugin, C. Malan, A. Mezzetti, J. Org. Chem. 2002, 67, 5239 and references cited therein;
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36
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During the course of this investigation, a highly selective unsymmetrical P-chiral bis(trialkylphosphane) ligand was prepared in both enantiomeric forms by Pfizer research group, but in small scale using chiral preparatory HPLC, see: G. Hoge, H.-P. Wu, W. S. Kissel, D. A. Pflum, D. J. Greene, J. Bao, J. Am. Chem. Soc. 2004, 126, 5966.
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Resolution of racemic phosphane oxide with (L)- or (D)-DBT was previously applied by Imamoto and Miura in the preparation of a dialkylaryl P-chiral phosphorus ligand, see: T. Miura, T. Imamoto, Tetrahedron Lett. 1999, 40, 4833. However, an attempt to resolve the corresponding racemic phosphane oxide intermediate of TangPhos failed due to the highly hygroscopic nature of that intermediate.
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48
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14944349858
-
-
note
-
tert-Butylphosphane was prepared on lab scale by reduction of commercially available tert-butyldichlorophosphane with LAH. It can also be prepared on industrial scale from phosphane and isobutene.
-
-
-
-
49
-
-
14944361924
-
-
note
-
For a representation of the X-ray crystallography of the complex of (-)-6 and (D)-DBT, see Supporting Information. The X-ray crystallography data of this complex has been deposited with the Cambridge Crystallographic Data Centre (CCDC-257476). Experimental details of the ligand synthesis and a general hydrogenation procedure are also available included in the Supporting Information.
-
-
-
-
50
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0037708569
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H.-J. Drexler, J. You, S. Zhang, C. Fischer, W. Baumann, A. Spannenberg, D. Heller, Org. Process Res. Dev. 2003, 7, 355 and references cited therein.
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Brown, J.M.1
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52
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14944367076
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-
note
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It was found that an ether solution of DuanPhos was exposed to air for overnight without any oxidation detected.
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