Journal of the American Chemical Society
Communication
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Scheme 1. Postulated Catalytic Cycle
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ability of alkenylnickel intermediates to undergo reversible E/Z
isomerization and have demonstrated the utility of this method
in promoting previously inaccessible domino reactions with high
enantioselectivities. We expect this underexplored mode of
reactivity may have significant untapped potential, and its
creative use in other contexts may lead to further new
applications in organic synthesis.7
ASSOCIATED CONTENT
* Supporting Information
The Supporting Information is available free of charge on the
■
S
Experimental procedures and full spectroscopic data for all
Crystallographic data (CIF)
Crystallographic data (CIF)
Crystallographic data (CIF)
Crystallographic data (CIF)
AUTHOR INFORMATION
Corresponding Author
■
Author Contributions
‡These authors contributed equally.
(8) The relative and absolute configurations of the products were
assigned by analogy with those of ent-2c, ent-2i, 7a, and 10 which were
determined by X-ray crystallography. See the SI for details.
Notes
The authors declare no competing financial interest.
(9) Partridge, B. M.; Solana Gonzal
Ed. 2014, 53, 6523.
́
ez, J.; Lam, H. W. Angew. Chem., Int.
ACKNOWLEDGMENTS
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(10) Miura, T.; Shimada, M.; Murakami, M. Angew. Chem., Int. Ed.
2005, 44, 7598.
We thank the ERC (Starting Grant no. 258580), EPSRC
(Leadership Fellowship to H.W.L.; grants EP/I004769/1 and
EP/I004769/2), the University of Nottingham, and GlaxoS-
mithKline for support of this work. We thank Dr. Benjamin M.
Partridge (University of Sheffield) for helpful suggestions. We
are grateful to Dr. William Lewis (University of Nottingham) for
X-ray crystallography.
(11) (a) von Matt, P.; Pfaltz, A. Angew. Chem., Int. Ed. Engl. 1993, 32,
566. (b) Sprinz, J.; Helmchen, G. Tetrahedron Lett. 1993, 34, 1769.
(c) Allen, J. V.; Coote, S. J.; Dawson, G. J.; Frost, C. G.; Martin, C. J.;
Williams, J. M. J. J. Chem. Soc., Perkin Trans. 1 1994, 2065.
(12) However, replacing ent-L6 with L3 did lead to productive
reactions with varying degrees of success. See the SI further details.
(13) (a) Shintani, R.; Okamoto, K.; Hayashi, T. Chem. Lett. 2005, 34,
1294. (b) Yang, M.; Zhang, X.; Lu, X. Org. Lett. 2007, 9, 5131.
(14) (a) Yamamoto, A.; Suginome, M. J. Am. Chem. Soc. 2005, 127,
15706. (b) Daini, M.; Yamamoto, A.; Suginome, M. Asian J. Org. Chem.
2013, 2, 968.
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