Journal of the American Chemical Society
COMMUNICATION
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We are grateful to the National Science Foundation for support
of this research (Grant CHE-0911192). M.C.H. acknowledges
Celgene for generous support through a Celgene Drug Discovery
Fellowship. We thank Dr. Tom Emge for crystallographic analysis.
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(15) While the results in Table 1 indicate that the catalyst pKa is
certainly important, there appears to be no direct correlation between
catalyst activity and acidity. Acids with similar pKa’s (e.g., DPP and
phosphoric acid) gave vastly different results. We thus speculate that
catalyst reactivity might be partially dependent on catalyst solubility in
the nonpolar reaction medium (or on the corresponding solubility of
protonated starting material/product).
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relatively complex starting materials via an intriguing gold-catalyzed
cascade reaction that involves a 1,5-hydride shift: Zhou, G.; Zhang,
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(17) No reduction of 17 was observed in the absence of 12a.
2103
dx.doi.org/10.1021/ja110713k |J. Am. Chem. Soc. 2011, 133, 2100–2103