Organic Letters
Letter
J. M.; Steel, P. J.; Whittington, B. I.; Battiste, M. A. J. Org. Chem.
1989, 54, 1383. (d) Coxon, J. M.; Steel, P. J.; Whittington, B. I. J.
Org. Chem. 1989, 54, 3702. (e) Meyer, C.; Blanchard, N.; Defosseux,
M.; Cossy, J. Acc. Chem. Res. 2003, 36, 766. (f) Defosseux, M.;
Blanchard, N.; Meyer, C.; Cossy, J. Tetrahedron 2005, 61, 7632.
(g) Raghavan, S.; Sudheer Babu, V.; Sridhar, B. J. Org. Chem. 2011,
76, 557.
(9) Selected references: (a) Albelo, G.; Wiger, G.; Rettig, M. F. J.
Am. Chem. Soc. 1975, 97, 4510. (b) Parra-Hake, M.; Rettig, M. F.;
Wing, R. M.; Woolcock, J. C. Organometallics 1982, 1, 1478. (c) He,
Z.; Yudin, A. K. Org. Lett. 2006, 8, 5829.
ASSOCIATED CONTENT
* Supporting Information
The Supporting Information is available free of charge on the
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S
Detailed experimental procedures and characterization
data for new compounds (PDF)
AUTHOR INFORMATION
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(10) Selected references: (a) Stewart, F. F.; Jennings, P. W. J. Am.
Chem. Soc. 1991, 113, 7037. (b) Stewart, F. F.; Neilsen, W. D.;
Ekeland, R. E.; Larsen, R. D.; Jennings, P. W. Organometallics 1993,
12, 4585.
Corresponding Author
ORCID
(11) Selected references: (a) South, A.; Ouellette, R. J. J. Am. Chem.
Soc. 1968, 90, 7064. (b) Ouellette, R. J.; Williams, S. J. Org. Chem.
1970, 35, 3210. (c) Kocovsky, P.; Srogl, J.; Pour, M.; Gogoll, A. J.
Am. Chem. Soc. 1994, 116, 186.
Author Contributions
The manuscript was written through contributions of all
authors. All authors have given approval to the final version of
the manuscript.
(12) Daniels, R. G.; Paquette, L. A. J. Org. Chem. 1981, 46, 2901.
(13) Rosner, C.; Hennecke, U. Org. Lett. 2015, 17, 3226.
̈
(14) Ke, Z.; Wong, Y.-C.; See, J. Y.; Yeung, Y.-Y. Adv. Synth. Catal.
2016, 358, 1719.
Notes
(15) Wong, Y.-C.; Ke, Z.; Yeung, Y.-Y. Org. Lett. 2015, 17, 4944.
(16) An exception to the modified Markownikoff’s rule is the
protonolysis of tricyclo[3.2.1.02,4]octane4i and tricyclo [3.2.2.02,4]
nonane4l systems, in which the proton addition preferentially takes
place at the most-substituted carbon of the cyclopropane.
(17) “Edge”4l and “corner”4d,i,l protonated cyclopropane transition
states have been postulated to explain the retention or inversion of
stereochemistry of the carbon attacked by the proton. Other
hypotheses propose an “edge” trajectory of the protonation as the
transition to the corner-protonated intermediate.4c,f,g
The authors declare no competing financial interest.
ACKNOWLEDGMENTS
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Financial support through an internal grant from the Latvian
Institute of Organic Synthesis is acknowledged. We thank
M.Sc. Martins Otikovs for assistance with 2D NMR spectra,
Dr. Anatoly Mishnov for performing X-ray analysis, and Dr.
Liene Grigorjeva for assistance in manuscript preparation.
REFERENCES
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