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c) For an extensive review on P,N Ligands with pyridine donors, see: G. Chelucci, G. Orru, G. A. Pinna, Tetrahedron 2003, 59, 9471-9515.
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Chelucci, G.1
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9344250383
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note
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Quinap: 1-(2-diphenylphosphino-1-naphthyl)isoquinoline.
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6
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9344222627
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note
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We suggest the acronym pinap in analogy to quinap, where "pi" refers to phthalazine.
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13
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0027408256
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N. W. Alock, J. M. Brown, D. I. Hulmes, Tetrahedron: Asymmetry 1993, 4, 743-756.
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15
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9344266174
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note
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50 mg (P)- or (M)-quinap costs € 143 at STREM.
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16
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0041507105
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M. Pal, V. R. Batchu, K. Parasuraman, K. Yeleswarapu, J. Org. Chem. 2003, 68, 6806-6809.
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17
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9344234254
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note
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Depending on the scale, different separation procedures were applied. Typically on > 2 g scale either 3a or 5a was selectively crystallized from the mixture (see Supporting Information for details), and the residue was purified by flash chromatography. On a smaller scale the diastereomers were separated by flash chromatography; for example, 1.21 g of a mixture of 3a/3b was separated by flash chromatography to give 3a (595 mg) and 3b (501 mg; 91% mass recovery).
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18
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9344258434
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note
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CCDC-243850 (3a) and CCDC-243851 (5a) contain the supplementary crystallographic data for this paper. These data can be obtained free of charge via www.ccdc.cam.ac.uk/conts/retrieving.html (or from the Cambridge Crystallographic Data Centre, 12, Union Road, Cambridge CB21EZ, UK; fax: (+44)1223-336-033; or deposit@ccdc.cam.ac.uk).
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Schnyder, A.1
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c) A. Schnyder, L. Hintermann, A. Togni, Angew. Chem. 1995, 107, 628-630; Angew. Chem. Int. Ed. Engl. 1995, 34, 931-933.
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23
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9344227173
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note
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Ligand 3b gave slightly lower enantioselectivities (89% ee in the hydroboration of styrene). The complexes with ligands 5a and 5b gave lower enantioselectivities and yields.
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24
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0037073234
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J. M. Longmire, B. Wang, X. Zhang, J. Am. Chem. Soc. 2002, 124, 13400-13401.
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25
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9344265011
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note
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Ligand 3b gave slightly lower enantioselectivities (93% ee for R = CN). The complexes with ligands 5a and 5b gave lower enantioselectivities and yields.
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26
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0041407526
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0005675924
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K. C. Brannock, R. D. Burpitt, J. G. Thweatt, J. Org. Chem. 1963, 28, 1462-1464.
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32
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9344262758
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note
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Ligands 3a and 3b gave comparable results (for R = iPr and R′ = Ph; 3a: 92% ee (R) and 3b: 94% ee (S)).
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