Organic Letters
Letter
M.; French, A. N.; Wirth, T. Synlett 2007, 2007, 538. (k) Hirt, U. H.;
Schuster, M. F. H.; French, A. N.; Wiest, O. G.; Wirth, T. Eur. J. Org.
Chem. 2001, 2001, 1569. (l) Hirt, U. H.; Spingler, B.; Wirth, T. J. Org.
Chem. 1998, 63, 7674. (m) Wirth, T.; Hirt, U. H. Tetrahedron:
Asymmetry 1997, 8, 23.
AUTHOR INFORMATION
■
Corresponding Author
Notes
(8) Beaulieu, S.; Legault, C. Y. Chem. - Eur. J. 2015, 21, 11206.
(9) Basdevant, B.; Legault, C. Y. Org. Lett. 2015, 17, 4918.
(10) (a) Gonzalez-de-Castro, A.; Xiao, J. J. Am. Chem. Soc. 2015, 137,
8206. (b) VanBrunt, M. P.; Ambenge, R. O.; Weinreb, S. M. J. Org.
Chem. 2003, 68, 3323. (c) Huang, B.; Gupton, J. T.; Hansen, K. C.;
Idoux, J. P. Synth. Commun. 1996, 26, 165. (d) Leanna, M. R.; Morton,
H. E. Tetrahedron Lett. 1993, 34, 4485. (e) Morton, H. E.; Leanna, M.
R. Tetrahedron Lett. 1993, 34, 4481. (f) Duncan, R.; Drueckhammer,
D. G. Tetrahedron Lett. 1993, 34, 1733. (g) Hsiao, C.-N.; Leanna, M.
R.; Bhagavatula, L.; DeLara, E.; Zydowski, T. M.; Morton, H. E. Synth.
Commun. 1990, 20, 3507.
The authors declare no competing financial interest.
ACKNOWLEDGMENTS
■
This work was supported by the National Science and
Engineering Research Council (NSERC) of Canada, the
Canada Foundation for Innovation (CFI), the FRQNT Centre
in Green Chemistry and Catalysis (CGCC), and the Universite
de Sherbrooke.
́
(11) De Kimpe, N.; Verhe, R. In The Chemistry of α-Haloketones, α-
Haloaldehydes and α-Haloimines; Patai, S., Rappoport, Z., Eds.; Wiley:
New York, 1988; p 496.
(12) (a) Trost, B. M.; Pinkerton, A. B. Tetrahedron Lett. 2000, 41,
9627. (b) Uenishi, J.; Kawahama, R.; Yonemitsu, O. J. Org. Chem.
1998, 63, 8965. (c) Roush, W. R.; Moriarty, K. J.; Brown, B. B.
Tetrahedron Lett. 1990, 31, 6509.
REFERENCES
■
(1) (a) Zhdankin, V. V. Hypervalent Iodine Chemistry: Preparation,
Structure, and Synthetic Applications of Polyvalent Iodine Compounds;
Wiley: Chichester, U.K., 2013. (b) Tohma, H.; Kita, Y. In Hypervalent
Iodine Chemistry; Wirth, T., Ed.; Springer: Berlin, 2003; p 209.
(c) Zhdankin, V. V.; Stang, P. J. Chem. Rev. 2002, 102, 2523.
(d) Moriarty, R. M.; Prakash, O. Org. React. 2001, 57, 327.
(e) Varvoglis, A. Hypervalent Iodine in Organic Synthesis; Academic
Press: San Diego, 1997.
(14) Basdevant, B.; Legault, C. Y. J. Org. Chem. 2015, 80, 6897.
(2) (a) Bosset, C.; Coffinier, R.; Peixoto, P. A.; El Assal, M.; Miqueu,
K.; Sotiropoulos, J.-M.; Pouysegu, L.; Quideau, S. Angew. Chem., Int.
́
Ed. 2014, 53, 9860. (b) Volp, K.; Harned, A. M. Chem. Commun. 2013,
49, 3001. (c) Uyanik, M.; Yasui, T.; Ishihara, K. Angew. Chem., Int. Ed.
2013, 52, 9215. (d) Uyanik, M.; Yasui, T.; Ishihara, K. Angew. Chem.,
Int. Ed. 2010, 49, 2175. (e) Uyanik, M.; Yasui, T.; Ishihara, K.
Tetrahedron 2010, 66, 5841. (f) Quideau, S.; Lyvinec, G.; Marguerit,
M.; Bathany, K.; Ozanne-Beaudenon, A.; Buffeteau, T.; Cavagnat, D.;
́ ́
Chenede, A. Angew. Chem., Int. Ed. 2009, 48, 4605. (g) Boppisetti, J.
K.; Birman, V. B. Org. Lett. 2009, 11, 1221. (h) Dohi, T.; Maruyama,
A.; Takenaga, N.; Senami, K.; Minamitsuji, Y.; Fujioka, H.;
Caemmerer, S. B.; Kita, Y. Angew. Chem., Int. Ed. 2008, 47, 3787.
(3) (a) Singh, F. V.; Wirth, T. Chem. - Asian J. 2014, 9, 950. (b) Dohi,
T.; Kita, Y. Chem. Commun. 2009, 2073. (c) Uyanik, M.; Ishihara, K.
Chem. Commun. 2009, 2086. (d) Zhdankin, V. V. ARKIVOC 2009, 1,
1. (e) Richardson, R. D.; Wirth, T. Angew. Chem., Int. Ed. 2006, 45,
4402. (f) Wirth, T. Angew. Chem., Int. Ed. 2005, 44, 3656.
(4) (a) Khanna, M. S.; Garg, C. P.; Kapoor, R. P. Tetrahedron Lett.
1992, 33, 1495. (b) Iodine(III) variant: Koser, G. F.; Relenyi, A. G.;
Kalos, A. N.; Rebrovic, L.; Wettach, R. H. J. Org. Chem. 1982, 47,
2487.
(5) Reviews on hypervalent iodine-mediated asymmetric trans-
formations: (a) Kumar, R.; Wirth, T. Top. Curr. Chem. 2015,
587. (c) Parra, A.; Reboredo, S. Chem. - Eur. J. 2013, 19, 17244.
(d) Ngatimin, M.; Lupton, D. W. Aust. J. Chem. 2010, 63, 653.
(6) Reviews on hypervalent iodine-mediated functionalization of
carbonyl compounds: (a) Dong, D.-Q.; Hao, S.-H.; Wang, Z.-L.; Chen,
C. Org. Biomol. Chem. 2014, 12, 4278. (b) Merritt, E. A.; Olofsson, B.
Synthesis 2011, 2011, 517.
(7) (a) Brenet, S.; Minozzi, C.; Clarens, B.; Amiri, L.; Berthiol, F.
Synthesis 2015, 47, 3859. (b) Brenet, S.; Berthiol, F.; Einhorn, J. Eur. J.
̀
́
Org. Chem. 2013, 2013, 8094. (c) Therien, M.-E.; Guilbault, A.-A.;
Legault, C. Y. Tetrahedron: Asymmetry 2013, 24, 1193. (d) Guilbault,
A.-A.; Basdevant, B.; Wanie, V.; Legault, C. Y. J. Org. Chem. 2012, 77,
11283. (e) Guilbault, A.-A.; Legault, C. Y. ACS Catal. 2012, 2, 219.
(f) Rodriguez, A.; Moran, W. J. Synthesis 2012, 44, 1178. (g) Yu, J.;
Cui, J.; Hou, X.-S.; Liu, S.-S.; Gao, W.-C.; Jiang, S.; Tian, J.; Zhang, C.
Tetrahedron: Asymmetry 2011, 22, 2039. (h) Farooq, U.; Schafer, S.;
̈
Shah, A. A.; Freudendahl, D. M.; Wirth, T. Synthesis 2010, 2010, 1023.
(i) Altermann, S. M.; Richardson, R. D.; Page, T. K.; Schmidt, R. K.;
Holland, E.; Mohammed, U.; Paradine, S. M.; French, A. N.; Richter,
C.; Bahar, A. M.; Witulski, B.; Wirth, T. Eur. J. Org. Chem. 2008, 2008,
5315. (j) Richardson, R. D.; Page, T. K.; Altermann, S. M.; Paradine, S.
D
Org. Lett. XXXX, XXX, XXX−XXX