Organic Letters
Letter
(10) Deuterated drugs: (a) Katsnelson, A. Nat. Med 2013, 19, 656.
Deuterated uracil derivatives: (b) Srinivas, G.; Unny, V. K. P.; Mukkanti,
K.; Choudary, B. M. Appl. Radiat. Isot. 2013, 72, 100. Deuteration using
AUTHOR INFORMATION
Corresponding Authors
■
Notes
́
SmI2-D2O: (c) Concellon, J. M.; Bernad, P. L.; Rodríguez-Solla, H.
Angew. Chem., Int. Ed. 2001, 40, 3897. (d) Davies, S. G.; Rodríguez-Solla,
H.; Tamayo, J. A.; Garner, A. C.; Smith, A. D. Chem. Commun. 2004,
2502.
The authors declare no competing financial interest.
(11) For a related 1,2-shift, see: (a) Nguyen, Q.; Nguyen, T.; Driver, T.
G. J. Am. Chem. Soc. 2013, 135, 620. Activation of Sm(II): (b) Szostak,
M.; Procter, D. J. Angew. Chem., Int. Ed. 2012, 51, 9238.
(12) (a) Burke, M. D.; Schreiber, S. L. Angew. Chem., Int. Ed. 2004, 43,
46. (b) Galloway, W. R. J. D.; Isidro-Llobet, A.; Spring, D. R. Nat.
Commun. 2010, 1, no. 80. (c) O’Connor, C. J.; Beckmann, H. S. G.;
Spring, D. R. Chem. Soc. Rev. 2012, 41, 4444.
ACKNOWLEDGMENTS
We thank the EPRSC for support.
■
REFERENCES
■
(1) (a) Brunton, L.; Chabner, B.; Knollman, B. Goodman and Gilman’s
The Pharmacological Basis of Therapeutics; McGraw-Hill: New York,
2010. (b) Bloomfield, V. A.; Crothers, D. M.; Tinoco, I. Nucleic Acids:
Structures, Properties and Functions; University Science Books: Sausalito,
CA, 2000.
(13) Szostak, M.; Sautier, B.; Procter, D. J. Chem. Commun. 2013,
DOI: 10.1039/C3CC48932A.
(2) Selected examples: (a) Hopkins, A. L.; Ren, J.; Tanaka, H.; Baba,
M.; Okamato, M.; Stuart, D. I.; Stammers, D. K. J. Med. Chem. 1999, 42,
4500. (b) Klein, R. S.; Lenzi, M.; Lim, T. H.; Hotchkiss, K. A.; Wilson,
P.; Schwartz, E. L. Biochem. Pharmacol. 2001, 62, 1257. (c) Fustero, S.;
Salavert, E.; Sanz-Cervera, J. F.; Piera, J.; Asensio, A. Chem. Commun.
2003, 844. (d) Kalman, T. I.; Lai, L. Nucleosides, Nucleotides Nucleic Acids
2005, 24, 367. (e) LaFrate, A. L.; Katzenellenbogen, J. A. J. Org. Chem.
2007, 72, 8573. (f) Novikov, M. S.; Ivanova, O. N.; Ivanov, A. V.;
Ozerov, A. A.; Valuev-Elliston, V. T.; Temburnikar, K.; Gurskaya, G. V.;
Kochetkov, S. N.; Pannecouque, C.; Balzarini, J.; Seley-Radtke, K. L.
Bioorg. Med. Chem. Lett. 2011, 19, 5794. (g) Liu, Y.; Lim, B. H.; Jiang, W.
W.; Flentge, C. A.; Hutchinson, D. K.; Madigan, D. L.; Randolph, J. T.;
Wagner, R.; Maring, C. J.; Kati, W. M.; Molla, A. Bioorg. Med. Chem. Lett.
2012, 22, 3747.
(3) (a) Bardagi, J. I.; Rossi, R. A. Org. Prep. Proc. Int. 2009, 41, 479.
(b) Joule, J. A.; Mills, K. Heterocyclic Chemistry; Wiley-Blackwell:
Oxford, 2010.
́
(4) Reviews: (a) Bojarski, J. T.; Mokrosz, J. L.; Barton, H. J.;
Paluchowska, M. H. Adv. Heterocycl. Chem. 1985, 38, 229. (b) Abraham,
D. J.; Rotella, D. P. Burger’s Medicinal Chemistry, Drug Discovery and
Development; Wiley: Hoboken, NJ, 2010. (c) Seeliger, F.; Berger, S. T.
A.; Remennikov, G. Y.; Polborn, K.; Mayr, H. J. Org. Chem. 2007, 72,
9170.
(5) Reviews: (a) Speckamp, W. N.; Moolenaar, M. J. Tetrahedron 2000,
56, 3817. (b) Maryanoff, B. E.; Zhang, H. C.; Cohen, J. H.; Turchi, I. J.;
Maryanoff, C. A. Chem. Rev. 2004, 104, 1431. (c) Yazici, A.; Pyne, S. G.
Synthesis 2009, 339. (d) Yazici, A.; Pyne, S. G. Synthesis 2009, 513.
(6) Selected examples: (a) Roper, S.; Wartchow, R.; Hoffmann, H. M.
̈
R. Org. Lett. 2002, 4, 3179. (b) Muratore, M. E.; Holloway, C. A.; Pilling,
A. W.; Storer, R. I.; Trevitt, G.; Dixon, D. J. J. Am. Chem. Soc. 2009, 131,
10796. (c) Breman, A. C.; Dijkink, J.; van Maarseveen, J. H.; Kinderman,
S. S.; Hiemstra, H. J. Org. Chem. 2009, 74, 6327. (d) Mentink, G.; van
Maarseveen, J. H.; Hiemstra, H. Org. Lett. 2002, 4, 3497. (e) Sun, H.;
Martin, C.; Kesselring, D.; Keller, R.; Moeller, K. D. J. Am. Chem. Soc.
2006, 128, 13761. (f) Raheem, I. T.; Thiara, P. S.; Peterson, E. A.;
Jacobsen, E. N. J. Am. Chem. Soc. 2007, 129, 13404.
(7) (a) Szostak, M.; Sautier, B.; Spain, M.; Behlendorf, M.; Procter, D.
J. Angew. Chem., Int. Ed. 2013, 52, 12559. (b) α-Hydroxy-N-
acylcarbamides were prepared using SmI2−H2O (dr 77:23 to 91:9).
The stereochemistry at the hemiaminal center has no bearing on the
stereochemical outcome of the additions.
(8) Reviews on SmI2: (a) Kagan, H. B. Tetrahedron 2003, 59, 10351.
(b) Molander, G. A.; Harris, C. R. Tetrahedron 1998, 54, 3321.
(c) Edmonds, D. J.; Johnston, D.; Procter, D. J. Chem. Rev. 2004, 104,
3371. (d) Nicolaou, K. C.; Ellery, S. P.; Chen, J. S. Angew. Chem., Int. Ed.
2009, 48, 7140. (e) Szostak, M.; Procter, D. J. Angew. Chem., Int. Ed.
2011, 50, 7737. (f) Szostak, M.; Spain, M.; Procter, D. J. Chem. Soc. Rev.
2013, 42, 9155.
(9) Recent applications of SmI2−H2O: (a) Szostak, M.; Spain, M.;
Procter, D. J. Chem. Commun. 2011, 47, 10254. (b) Szostak, M.; Spain,
M.; Procter, D. J. Org. Lett. 2012, 14, 840.
455
dx.doi.org/10.1021/ol403340j | Org. Lett. 2014, 16, 452−455