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. 2013 Aug 26;52(35):9153-6.
doi: 10.1002/anie.201303994. Epub 2013 Jul 10.

Nickel-catalyzed enantioselective arylation of pyridinium ions: harnessing an iminium ion activation mode

Stephen T Chau  1 , J Patrick Lutz, Kevin Wu, Abigail G Doyle
Affiliations

Nickel-catalyzed enantioselective arylation of pyridinium ions: harnessing an iminium ion activation mode

Stephen T Chau et al. Angew Chem Int Ed Engl. .
No abstract available

Keywords: Negishi reaction; asymmetric catalysis; cross-coupling; nickel; nitrogen heterocycles.

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Figures

Figure 1
Figure 1
Solid-state structure of allyl NiII complex 3. Ellipsoids set at 30% probability. Hydrogen atoms omitted for clarity.
Scheme 1
Scheme 1
Nickel-catalyzed cross-coupling with iminium ions.
Scheme 2
Scheme 2
Scope of aryl zinc nucleophiles in the reaction. Yields and ee values are the average of two runs on a 0.5 mmol scale. [a] Yield and ee after recrystallization from ether. [b] Reaction warmed to RT. [c] Reaction warmed to −20°C. [d] Derived from an ArZnCl solution (0.3Min THF). [f] Reaction warmed to −50°C.
Scheme 3
Scheme 3
Stoichiometric reaction between Ni0 and a pyridinium ion.
Scheme 4
Scheme 4
Proposed catalytic cycle.
See this image and copyright information in PMC

References

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    1. Graham TJA, Shields JD, Doyle AG. Chem Sci. 2011;2:980–985.
    1. Graham TJA, Doyle AG. Org Lett. 2012;14:1616–1619. - PMC - PubMed
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    1. For some recent examples of the use of 4-piperidones in the synthesis of biologically active 4-piperidines, see: Tawara JN, Lorenz P, Stermitz FR. J Nat Prod. 1999;62:321–323.Watson PS, Jiang B, Scott B. Org Lett. 2000;2:3679–3681.Brooks CA, Comins DL. Tetrahedron Lett. 2000;41:3551–3553.

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