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in regio- and enantioselectivity. More importantly, the present
work highlights the potential of ionic interactions with charged
catalysts as a strategy for rapid assembly and assessment of
cooperative effects between supports and chiral homogeneous
catalysts for the develop of heterogeneous asymmetric catalysts.
ASSOCIATED CONTENT
* Supporting Information
■
S
Am. Chem. Soc. 2003, 125, 14982−14983.
Rh-catalyzed hydro-
Details of experimental procedures, NMR spectra, and
spectroscopic data. The Supporting Information is available
forymylation: (c) Bianchini, C.; Burnaby, D. G.; Evans, J.; Frediani, P.;
Meli, A.; Oberhauser, W.; Psaro, R.; Sordelli, L.; Vizza, F. J. Am. Chem.
Soc. 1999, 121, 5961−5971. Cu-catalyzed alkynylation reactions:
(d) McDonagh, C.; O’Conghaile, P.; Gebbink, R. J. M. K.; O’Leary, P.
Tetrahedron Lett. 2007, 48, 4387−4390. Diels−Alder reactions:
(e) Wang, H.; Liu, X.; Xia, H.; Liu, P.; Gao, J.; Ying, P.; Xiao, J.; Li, C.
Tetrahedron 2006, 62, 1025−1032.
AUTHOR INFORMATION
Corresponding Authors
■
(9) For alternative approaches to enantioselective heterogeneous
gold catalysis, see: (a) Gross, E.; Liu, J. K.; Alayoglu, S.; Marcus, M. A.;
Fakra, S. C.; Toste, F. D.; Somorjai, G. A. J. Am. Chem. Soc. 2013, 135,
3881−3886. For recent reviews on enantioselective heterogeneous
catalysis, see: (b) Yasukawa, T.; Miyamura, H.; Kobayashi, S. Chem.
Soc. Rev. 2014, 43, 1450−1461. (c) Fraile, J. M.; Garcia, J. I.; Herrerias,
C. I.; Mayoral, J. A.; Pires, E. Chem. Soc. Rev. 2009, 38, 605−706.
(10) Wiench, J. W.; Michon, C.; Ellern, A.; Hazendonk, P.; Iuga, A.;
Angelici, R. J.; Pruski, M. J. Am. Chem. Soc. 2009, 131, 11801−11810.
Notes
The authors declare no competing financial interest.
ACKNOWLEDGMENTS
■
We thank the financial support from the Dow Chemical
Company through funding for the Core−Shell Catalysis
Project, Contract No. 20120984 to University of California,
Berkeley. We are grateful to Dr. David Barton, Dr. Pete Nickias,
and Dr. Trevor Ewers from Dow Chemical Co.; Dr. Elad Gross
and Juncong Jiang for useful discussions; Julia Oktawiec for the
nitrogen adsorption−desorption isotherms; and Rong Ye for
Inductively Coupled Plasma Optical Emission Spectroscopy
(ICP-OES) analysis.
(11) Brown, T. J.; Weber, D.; Gagne,
Am. Chem. Soc. 2012, 134, 9134−9137.
(12) See Supporting Information for control experiments examining
the accelerating effect of a Brønsted acid (Figure S7).
́
M. R.; Widenhoefer, R. A. J.
(13) Gross, E.; Liu, J. H.; Toste, F. D.; Somorjai, G. A. Nat. Chem.
2012, 4, 947−952.
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