Organic Letters
Letter
Bellucci, M. C.; Volonterio, A.; Zanda, M. Eur. J. Org. Chem. 2009, 35,
6179. (j) Fujiwara, S.-I.; Matsuya, T.; Maeda, H.; Shin-Ike, T.; Kambe,
N.; Sonoda, N. Synlett 1999, 1, 75. (k) Wiese, S.; Aguila, M. J. B.; Kogut,
E.; Warren, T. H. Organometallics 2013, 32, 2300. (l) Ito, Y.; Nirao, T.;
Saegusa, T. J. Org. Chem. 1975, 40, 2981. (m) Tucker, H. U. B.; Sayigh,
A. A. R. J. Am. Chem. Soc. 1972, 94, 3484. (n) Dondoni, A.; Barbaro, G.;
Battaglia, A. J. Org. Chem. 1977, 42, 3372. (o) Mindiola, D. J.; Hillhouse,
G. L. Chem. Commun. 2002, 38, 1840.
ACKNOWLEDGMENTS
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We gratefully acknowledge the Natural Science Foundation of
China (21172162, 21372174), the Young National Natural
Science Foundation of China (No. 21202111), the Ph.D.
Programs Foundation of Ministry of Education of China
(2013201130004), the Young Natural Science Foundation of
Jiangsu Province (BK2012174), PAPD, Key Laboratory of
Organic Synthesis of Jiangsu Province (KJS1211), and Soochow
University for financial support.
(7) (a) Pri-Bar, I.; Schwartz, J. Chem. Commun. 1997, 33, 327.
(b) Vlaar, T.; Cioc, R. C.; Mampuys, P.; Maes, B. U. W.; Orru, R. V. A.;
Ruijter, E. Angew. Chem., Int. Ed. 2012, 51, 13058.
(8) (a) Lazar, M.; Angelici, R. J. J. Am. Chem. Soc. 2006, 128, 10613.
(b) Angelici, R. J.; Lazar, M. Inorg. Chem. 2008, 47, 9155.
(9) Zhu, T.-H.; Wang, S.-Y.; Tao, Y.-Q.; Wei, T.-Q.; Ji, S.-J. Org. Lett.
2014, 16, 1260.
(10) (a) Du, Z.; Li, W.-B.; Zhu, X.-H.; Xu, F.; Shen, Q. J. Org. Chem.
2008, 73, 8966. (b) Zhang, X.-M.; Wang, C.-Y.; Qian, C.-W.; Han, F.-B.;
Xu, F.; Shen, Q. Tetrahedron 2011, 67, 8790. (c) Li, Z.; Xue, M.-Q.; Yao,
H.-S.; Sun, H.-M.; Zhang, Y.; Shen, Q. J. Organomet. Chem. 2012, 713,
27.
(11) Anderson, J. C.; Bou-Moreno, R. Tetrahedron 2010, 66, 9182.
(12) Li, W.-J.; Li, Q.; Liu, D.-L.; Ding, M.-W. J. Agric. Food Chem. 2013,
61, 1419.
(13) (a) Kuehle, E.; Anders, B.; Zucmach, G. Angew. Chem., Int. Ed.
1967, 6, 649. (b) Kaim, El. L.; Grimaud, L.; Patil, P. Org. Lett. 2011, 13,
1261. (c) Currie, K. S.; Tennant, G. J. Chem. Soc. Chem. Commum. 1995,
2295. (d) Yu, H.; Zhang, M.-S.; Sun, W.-L.; Li, Y.-Z.; Gao, R. Lett. Org.
Chem. 2010, 7, 566. (e) Yu, H.; Li, Y.-Z.; Liu, Q.; Zhang, M.-S.; Sun, W.-
L. Chin. Chem. Lett. 2012, 23, 130.
REFERENCES
■
(1) (a) Khorana, H. G. Chem. Rev. 1953, 53, 145. (b) Kurzer, F.;
Douraghi-Zadeh, K. Chem. Rev. 1967, 67, 107. (c) Williams, A.; Ibrahim,
I. T. Chem. Rev. 1981, 81, 589. (d) Zeni, G.; Larock, R. C. Chem. Rev.
2006, 106, 4644. (e) El-Faham, A.; Albericio, F. Chem. Rev. 2011, 111,
6557.
(2) (a) Mukumoto, K.; Nojima, T.; Takenaka, S. Nucleic Acids Symp.
Ser. 2004, 48, 251. (b) Tian, G.-L.; Lu, Y.-J.; Novak, B. M. J. Am. Chem.
Soc. 2004, 126, 4082. (c) Monagle, J. J. J. Org. Chem. 1962, 27, 3851.
(d) Sheehan, J. C.; Hess, G. P. J. Am. Chem. Soc. 1955, 77, 1067.
(e) Wendlberger, G. Houben-Weyl: Methoden der Organischen Chemie;
Georg Thieme Verlag: Stuttgart, 1974; Vol. 15/2, p 101. (f) Podlech, J.
In Houben-Weyl Methods of Organic Chemistry. Synthesis of Peptides and
Peptidomimetics; Goodman, M., Felix, A., Moroder, L., Toniolo, C., Eds.;
Thieme-Verlag: Stuttgart, 2001; Vol. E22a, pp 517−533. (g) Pozo, C.;
Keller, A. I.; Nagashima, T.; Curran, D. P. Org. Lett. 2007, 9, 4167.
(h) Sureshbabu, V. V.; Lalithamba, H. S.; Narendra, N.; Hemantha, H. P.
Org. Biomol. Chem. 2010, 8, 835. (i) Reagents for Glycoside, Nucleotide,
and Peptide Synthesis; Crich, D., Ed.; Wiley: New York, 2005. (j) Tan, D.;
Mottillo, C.; Katsenis, A. D.; Strukil, V.; Friscic, T. Angew. Chem., Int. Ed.
2014, 53, 9321.
(3) For recent selected examples, see: (a) Zeng, F.-L.; Alper, H. Org.
Lett. 2010, 12, 1188. (b) Roberts, B.; Liptrot, D.; Luker, T.; Stocks, M. J.;
Barber, C.; Webb, N.; Dods, R.; Martin, B. Tetrahedron Lett. 2011, 52,
3793. (c) Yuan, G.-D.; Liu, H.-Q.; Gao, J.-L.; Yang, K.-J.; Niu, Q.-S.;
Mao, H.; Wang, X.-X.; Lv, X. J. Org. Chem. 2014, 79, 1749. (d) Lv, X.;
Bao, W.-L. J. Org. Chem. 2009, 74, 5618. (e) Wang, F.; Cai, S.-J.; Liao,
Q.; Xi, C.-J. J. Org. Chem. 2011, 76, 3174. (f) Larksarp, C.; Alper, H. J.
Org. Chem. 1998, 63, 6229.
(4) (a) Qiu, G.; Liu, G.; Pu, S.; Wu, J. Chem. Commun. 2012, 48, 2903.
(b) Qiu, G.; Lu, Y.; Wu, J. Org. Biomol. Chem. 2013, 11, 798. (c) Qiu, G.;
He, Y.; Wu, J. Chem. Commun. 2012, 48, 3836.
(5) For recent selected examples, see: (a) Ding, M.-W.; Xu, Z.-F.; Wu,
T.-J. Synth. Commun. 1999, 29, 1171. (b) Ding, M.-W.; Zeng, G.-P.; Wu,
T.-J. Synth. Commun. 2000, 30, 1599. (c) Ding, M.-W.; Xu, Z.-F.; Liu, Z.-
J.; Wu, T.-J. Synth. Commun. 2001, 31, 1053. (e) Ding, M.-W.; Xu, S.-Z.;
Zhao, J.-F. J. Org. Chem. 2004, 69, 8366. (f) Zhao, J.-F.; Xie, C.; Xu, S.-Z.;
Ding, M.-W.; Xiao, W.-J. Org. Biomol. Chem. 2006, 4, 130. (g) Liu, M.-
G.; Hu, Y.-G.; Ding, M.-W. Tetrahedron 2008, 64, 9052. (h) He, P.; Wu,
J.; Nie, Y.-B.; Ding, M.-W. Tetrahedron 2009, 65, 8563. (i) Li, W.-J.; Liu,
S.; He, P.; Ding, M.-W. Tetrahedron 2010, 66, 8151. (j) Liu, H.; Wang,
H.-Q.; Ding, M.-W.; Liu, Z.-J.; Xiao, W.-J. J. Fluorine Chem. 2006, 127,
1584. (k) Liu, J.-C.; He, H.-W.; Ren, Q.-Y.; Ding, M.-W. Helv. Chim.
Acta 2006, 89, 1337. (l) Ding, M.-W.; Chen, Y.-F.; Huang, N.-Y. Eur. J.
Org. Chem. 2004, 3872. (m) Huang, N.-Y.; Liang, Y.-J.; Ding, M.-W.; Fu,
L.-W.; He, H.-W. Bioorg. Med. Chem. Lett. 2009, 19, 831. (n) Hua, Y.-G.;
Wang, Y.; Du, S.-M.; Chen, X.-B.; Ding, M.-W. Bioorg. Med. Chem. Lett.
2010, 20, 6188.
(6) (a) Schmittel, M.; Steffen, J.-P.; Rodriguez, D.; Engelen, B.;
Neumann, E.; Cinar, M. E. J. Org. Chem. 2008, 73, 3005. (b) Alajarin, M.;
Bonillo, B.; Ortin, M.-M.; Sanchez-Andrada, P.; Vidal, A. Org. Lett. 2006,
8, 5645. (c) Vicente, J.; Abad, J.-A.; Lopez-Serrano, J.; Jones, P. G.
Organometallics 2004, 23, 4711. (d) Anderson, J. C.; Bou-Moreno, R.
Tetrahedron 2010, 66, 9182. (e) Babcock, J. R.; Sita, L. R. J. Am. Chem.
Soc. 1998, 120, 5585. (f) Koketsu, M.; Suzuki, N.; Ishihara, H. J. Org.
Chem. 1999, 64, 6473. (g) Kim, S.; Yi, K.-Y. J. Org. Chem. 1986, 51, 2613.
(h) Kim, S.; Yi, K.-Y. Tetrahedron Lett. 1985, 26, 1661. (i) Olimpieri, F.;
1977
Org. Lett. 2015, 17, 1974−1977