Journal of the American Chemical Society
COMMUNICATION
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In summary, a novel approach to stereochemically dense
cyclohexenyl rings from terminal olefins has been achieved using
Pd(II)/sulfoxide CÀH activation catalysis. This dehydrogena-
tive DielsÀAlder reaction underscores the power of coupling
transition-metal-catalyzed CÀH activation to complexity-gener-
ating transformations for the rapid synthesis of complex molec-
ular skeletons from topologically simple starting materials.
Further investigations are focused on expanding the scope of
this transformation with respect to both the olefin class and
dienophile, and will be reported in due course.
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’ ASSOCIATED CONTENT
S
Supporting Information. Experimental procedures and
b
characterization data. This material is available free of charge via
’ AUTHOR INFORMATION
(14) (a) Young, A. J.; White, M. C. J. Am. Chem. Soc. 2008, 130,
14090. (b) Young, A. J.; White, M. C. Angew. Chem., Int. Ed. 2011,
50, 6824. (c) Lin, S.; Song, C.-X.; Cai, G.-X.; Wang, W.-H.; Shi, Z.-J.
J. Am. Chem. Soc. 2008, 130, 12901.
Corresponding Author
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’ ACKNOWLEDGMENT
Financial support was provided by NIH/NIGMS (grant no.
GM076153). E.M.S. is the recipient of a Bristol-Myers Squibb
graduate fellowship. We thank Johnson Matthey for a gift of
Pd(OAc)2 and Aldrich for a gift of catalyst 1. We also thank
Shauna Paradine for checking the experimental procedure for the
conversion of 28 to 29 in Scheme 3.
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dx.doi.org/10.1021/ja2059704 |J. Am. Chem. Soc. 2011, 133, 14892–14895