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bis(boronate) esters. Furthermore, the described route provides
a useful method for constructing 1,2-bis(boronates) with a
broad substrate scope.
ASSOCIATED CONTENT
* Supporting Information
Procedures, characterization and spectral data. This material is
■
S
AUTHOR INFORMATION
Corresponding Author
■
(9) (a) Kliman, L. T.; Mlynarski, S. N.; Ferris, G. E.; Morken, J. P.
Angew. Chem., Int. Ed. 2012, 51, 521. (b) Hong, K.; Morken, J. P. J.
Org. Chem. 2011, 76, 9102. (c) Burks, H. E.; Kliman, L. T.; Morken, J.
P. J. Am. Chem. Soc. 2009, 131, 9134. See also (d) Schuster, C. H.; Li,
B.; Morken, J. P. Angew. Chem., Int. Ed. 2011, 50, 7906.
Notes
The authors declare no competing financial interest.
ACKNOWLEDGMENTS
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(10) Hong, K.; Morken, J. P. J. Am. Chem. Soc. 2013, 135, 9252.
(11) (a) Lesley, G.; Nguyen, P.; Taylor, N. J.; Marder, T. B.; Scott, A.
J.; Clegg, W.; Norman, N. C. Organometallics 1996, 15, 5137.
(12) For example, deborylative alkylation of simple geminal
bis(boronates) is ineffective with NaOtBu in toluene. See ref 3a.
(13) Analogous orbital interactions have been claimed to explain the
stereoselectivity of reactions of allylsilanes, allylstannanes, and allyl
boronates. See: (a) Fleming, I.; Lawrence, N. J. Tetrahedron Lett. 1988,
29, 2073. (b) Fleming, I.; Lawrence, N. J. Tetrahedron Lett. 1988, 29,
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(e) Kyne, R. E.; Ryan, M. C.; Kliman, L. T.; Morken, J. P. Org. Lett.
2010, 12, 3796.
J.R.C. is grateful for a LaMattina Graduate Fellowship. The
NIH (GM-59471) is acknowledged for financial support.
AllyChem is acknowledged for a donation of B2(pin)2.
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■
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