Journal of the American Chemical Society
Communication
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(12) Additional bases, ligands, and TESOTf as an additive were
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(15) The absolute configuration for starting material and product was
determined for Table 2, entries 1 and 8, based on a comparison of
optical rotations to literature values or X-ray crystallography. For full
details, see the Supporting Information.
(16) Beesley, R. M.; Ingold, C. K.; Thorpe, J. F. J. Chem. Soc. Trans.
1915, 107, 1080−1106.
(17) Greene, M. A. Diastereoselective Synthesis of Seven Membered
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of California, Irvine, May 2013.
(18) Alternative tether lengths, for example, to generate the
corresponding 3-, 4-, or 6-membered methylenecycloalkanes, do not
provide desired products. For a summary of substrate classes that resist
Heck cyclization, see the Supporting Information.
(19) For a recent example of an intramolecular palladium-catalyzed
alkyne insertion/Suzuki reaction of alkyl iodides and aryl boronic
esters, see: Monks, B. A.; Cook, S. P. J. Am. Chem. Soc. 2012, 134,
15297−15300.
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Rev. 2000, 206−207, 199−235. For selected examples, see: (b) Tanke,
R. S.; Crabtree, R. H. J. Am. Chem. Soc. 1990, 112, 7984−7989.
(c) Chung, L. W.; Wu, Y.-D.; Trost, B. M.; Ball, Z. T. J. Am. Chem. Soc.
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(23) Faulkner, J. D. Synthesis 1971, 4, 175−189.
(24) Ojima, I. Catalytic Asymmetric Synthesis, 2nd ed.; Wiley and
Sons, Inc.: New York, 2005.
(25) Iimura, S.; Overman, L. E.; Paulini, R.; Zakarian, A. J. Am. Chem.
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(26) For details, see the Supporting Information.
ASSOCIATED CONTENT
■
S
* Supporting Information
Experimental procedures and characterization data for all new
compounds. This material is available free of charge via the
AUTHOR INFORMATION
■
Corresponding Author
Notes
The authors declare no competing financial interest.
ACKNOWLEDGMENTS
■
This work was supported by NIH NIGMS (R01GM100212),
the University of California (Chancellor’s Fellowship to
M.R.H.), the Ford Family Foundation (predoctoral fellowship
to M.R.H.), and the National Science Foundation (Graduate
Research Fellowship Grant Number DGE-1321846 to M.R.H.).
Dr. Joseph Ziller is acknowledged for X-ray crystallographic
analysis. Dr. Ivelina Yonova is thanked for helpful discussions.
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