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Upon screening other commonly used ligands for copper such as dimethyl ethylenediamine, BINAP or bisoxazolines, it was found that the use of Ph3P was crucial for achieving good yield and high anti selectivity.
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3P provided anti-2b in lower yield due to the formation of 3 (8%) and 4 (7%) in the reaction mixture.
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The anti stereochemistry of the ring-opened products was assigned by comparison of their NMR data with those of the reported compounds anti-2a, anti-2b (see ref. 26), and anti-9a and anti-9g (see ref. 21).
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(c) For previous ring opening of substrate 11, see reference 16.
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Matsuumi, M.2
Murugesh, M.G.3
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N2′ selectivity. For an excellent review on reaction mechanisms of organocuprate reagents in organic transformations, see: (a) Nakamura, E.; Mori, S. Angew. Chem. Int. Ed. 2000, 39, 3750.
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Nakamura, E.1
Mori, S.2
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(b) See also: Karlström, A. S. E.; Bäckvall, J.-E. In Modern Organocopper Chemistry; Krause, N., Ed.; Wiley-VCH: Weinheim, 2002, 259.
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Karlström, A.S.E.1
Bäckvall, J.-E.2
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Krause, N., Ed.; Wiley-VCH: Weinheim
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See also: Breit, B.; Demel, P. In Modern Organocopper Chemistry; Krause, N., Ed.; Wiley-VCH: Weinheim, 2002, 188-223.
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Breit, B.1
Demel, P.2
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33645961248
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note
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2Zn (1,2-dichloroethane, reflux), instead of EtMgBr, afforded exclusively the product syn-22b with only 20% conversion after 48 h (Figure 1), evidencing the key role exerted by the Grignard reagent in achieving both high reactivity and anti-stereocontrol. (Diagram presented)
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Diltz, S.; Aguirre, G.; Ortega, F.; Walsh, P. Tetrahedron: Asymmetry 1997, 21, 3559.
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Tetrahedron: Asymmetry
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Diltz, S.1
Aguirre, G.2
Ortega, F.3
Walsh, P.4
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