Organic Letters
Letter
(7) Chabardes, P.; Kuntz, E.; Varagnat, J. Tetrahedron 1977, 33, 1775.
(8) (a) Morrill, C.; Beutner, G. L.; Grubbs, R. H. J. Org. Chem. 2006,
71, 7813. (b) Morrill, C.; Grubbs, R. H. J. Am. Chem. Soc. 2005, 127,
2842. (c) Bellemin-Laponnaz, S.; Le Ny, J. P.; Osborn, J. A.
Tetrahedron Lett. 2000, 41, 1549. (d) Bellemin-Laponnaz, S.; Le Ny,
J. P.; Dedieu, A. Chem. - Eur. J. 1999, 5, 57. (e) Bellemin-Laponnaz, S.;
Gisie, H.; Le Ny, J. P.; Osborn, J. A. Angew. Chem., Int. Ed. Engl. 1997,
36, 976.
derived from aliphatic aldehydes proved generally unreactive.
Finally, propargylic alcohols derived from unsaturated
aldehydes underwent 1,3-allylic transposition reactions as
expected, and in one instance, the α,β,γ,δ-unsaturated acylsilane
could be obtained.
ASSOCIATED CONTENT
* Supporting Information
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S
(9) For a review on rhenium-catalyzed [1,3]-transposition of allylic
alcohols, see: Volchkov, I.; Lee, C. Chem. Soc. Rev. 2014, 43, 4381.
The Supporting Information is available free of charge on the
General experimental procedures and characterization
1
data, including H, 13C, 29Si, and 19F NMR, IR, and
AUTHOR INFORMATION
Corresponding Author
■
Notes
The authors declare no competing financial interest.
ACKNOWLEDGMENTS
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We gratefully acknowledge support of our work by the Natural
Science and Engineering Research Council of Canada
(NSERC) through a Discovery grant and Boehringer-Ingelheim
Canada through an unrestricted grant. We thank Professor
Michael Organ of York University for generous sharing of
resources and Dr. Howard Hunter of York University for
assistance with NMR experiments.
REFERENCES
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(1) Seminal report: (a) Brook, A. G. J. Am. Chem. Soc. 1958, 80,
1886. Account: (b) Brook, A. G. Acc. Chem. Res. 1974, 7, 77.
(2) For strategic applications of the Brook rearrangement in tandem
or cascade processes, see: (a) Boyce, G. R.; Greszler, S. N.; Johnson, J.
S.; Linghu, X.; Malinowski, J. T.; Nicewicz, D. A.; Satterfield, A. D.;
Schmitt, D. C.; Steward, K. M. J. Org. Chem. 2012, 77, 4503.
(b) Takeda, K.; Sasaki, M. Org. Synth. 2012, 89, 267. (c) Smith, A. B.,
III; Wuest, W. M. Chem. Commun. 2008, 5883. (d) Moser, W. H.
Tetrahedron 2001, 57, 2065. (e) Jankowski, P.; Raubo, P.; Wicha, J.
Synlett 1994, 1994, 985. (f) Kuwajima, I. J. Organomet. Chem. 1985,
285, 137.
(3) Reviews: (a) Zhang, H.-J.; Priebbenow, D. L.; Bolm, C. Chem.
Soc. Rev. 2013, 42, 8540. (b) Page, P. C. B.; McKenzie, M. J.; Klair, S.
S.; Rosenthal, S. Acyl silanes. In The Chemistry of Organosilicon
Compounds, Part 2; Patai, S., Rappoport, Z., Eds.; Wiley: Chichester,
1998; Vol. 2, p 1599. (c) Najera, C.; Yus, M. Org. Prep. Proced. Int.
1995, 27, 383. (d) Cirillo, P. F.; Panek, J. S. Org. Prep. Proced. Int.
1992, 24, 553. (e) Page, P. C. B.; Klair, S. S.; Rosenthal, S. Chem. Soc.
Rev. 1990, 19, 147. (f) Ricci, A.; Degl’Innocenti, A. Synthesis 1989, 9,
647.
(4) Seminal report: (a) Meyer, K. H.; Schuster, K. Ber. Dtsch. Chem.
Ges. B 1922, 55, 819. Reviews: (b) Cadierno, V.; Crochet, P.; Garcia-
Garrido, S. E.; Gimeno, J. Dalton Trans. 2010, 39, 4015. (c) Engel, D.
A.; Dudley, G. B. Org. Biomol. Chem. 2009, 7, 4149. (d) Swaminathan,
S.; Narayanan, K. V. Chem. Rev. 1971, 71, 429.
(5) For other syntheses of acylsilanes from silylated terminal alkynes,
see: (a) Miller, J. A.; Zweifel, G. Synthesis 1981, 288. (b) Horiuchi, Y.;
Taniguchi, M.; Oshima, K.; Utimoto, K. Tetrahedron Lett. 1995, 36,
5353.
(6) Two reports by the same group using this method include the
same example: (a) Narasaka, K.; Kusama, H.; Hayashi, Y. Chem. Lett.
1991, 1413. (b) Narasaka, K.; Kusama, H.; Hayashi, Y. Tetrahedron
1992, 48, 2059.
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