Organic Letters
Letter
(25) (a) Schmalisch, S.; Mahrwald, R. Org. Lett. 2013, 15, 5854.
(b) Kimura, T.; Eto, T.; Takahashi, D.; Toshima, K. Org. Lett. 2016, 18,
3190.
(26) McCooey, S. H.; Connon, S. J. Angew. Chem., Int. Ed. 2005, 44,
6367.
ASSOCIATED CONTENT
* Supporting Information
The Supporting Information is available free of charge on the
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S
(27) Ye, J. X.; Dixon, D. J.; Hynes, P. S. Chem. Commun. 2005, 4481.
(28) Liu, T. Y.; Cui, H. L.; Chai, Q.; Long, J.; Li, B. J.; Wu, Y.; Ding, L.
S.; Chen, Y. C. Chem. Commun. 2007, 2228.
(29) Palacio, C.; Connon, S. J. Chem. Commun. 2012, 48, 2849.
(30) Curti, C.; Rassu, G.; Zambrano, V.; Pinna, L.; Pelosi, G.; Sartori,
A.; Battistini, L.; Zanardi, F.; Casiraghi, G. Angew. Chem., Int. Ed. 2012,
51, 6200.
Experimental procedures and characterization data (PDF)
AUTHOR INFORMATION
Corresponding Author
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(31) Okino, T.; Hoashi, Y.; Takemoto, Y. J. Am. Chem. Soc. 2003, 125,
12672.
(32) Herrera, R. P.; Sgarzani, V.; Bernardi, L.; Ricci, A. Angew. Chem.,
Int. Ed. 2005, 44, 6576.
Author Contributions
∥S.M. and M.H. contributed equally
Notes
(33) Lubkoll, J.; Wennemers, H. Angew. Chem., Int. Ed. 2007, 46, 6841.
(34) Hamza, A.; Schubert, G.; Soos, T.; Papai, I. J. Am. Chem. Soc. 2006,
128, 13151.
(35) Wu, W. Q.; Min, L.; Zhu, L. Z.; Lee, C. S. Adv. Synth. Catal. 2011,
353, 1135.
(36) Vakulya, B.; Varga, S.; Csampai, A.; Soos, T. Org. Lett. 2005, 7,
1967.
(37) Kotke, M.; Schreiner, P. R. Tetrahedron 2006, 62, 434.
(38) Cheng, Y. A.; Yu, W. Z.; Yeung, Y. Y. Angew. Chem., Int. Ed. 2015,
54, 12102.
(39) Li, H. M.; Wang, Y.; Tang, L.; Deng, L. J. Am. Chem. Soc. 2004,
126, 9906−9907.
(40) Kendale, J. C.; Valentin, E. M.; Woerpel, K. A. Org. Lett. 2014, 16,
3684.
(41) Flock, A. M.; Krebs, A.; Bolm, C. Synlett 2010, 2010, 1219.
(42) Oh, J. S.; Lee, J. W.; Ryu, T. H.; Lee, J. H.; Song, C. E. Org. Biomol.
Chem. 2012, 10, 1052.
(43) Oh, S. H.; Rho, H. S.; Lee, J. W.; Lee, J. E.; Youk, S. H.; Chin, J.;
Song, C. E. Angew. Chem., Int. Ed. 2008, 47, 7872.
(44) Rho, H. S.; Oh, S. H.; Lee, J. W.; Lee, J. Y.; Chin, J.; Song, C. E.
Chem. Commun. 2008, 1208.
The authors declare no competing financial interest.
ACKNOWLEDGMENTS
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E.I.B. thanks EPSRC EP/G036764/1. M.C.G. thanks EPSRC
CAF EP/L001926/1, EP/J002542/1, and ERC-COG: 648239
for funding. E.M.M. thanks SFI and M. Curie COFUND (11/
SIRG/B2154).
REFERENCES
■
(1) Galan, M. C.; Dumy, P.; Renaudet, O. Chem. Soc. Rev. 2013, 42,
4599.
(2) Galan, M. C.; Benito-Alifonso, D.; Watt, G. M. Org. Biomol. Chem.
2011, 9, 3598.
(3) Varki, A.; Lowe, J. B. In Essentials of glycobiology; Varki, A., Ed.; Cold
Spring Harbor Laboratory Press: 2009.
(4) Corfield, A. P. In Glycobiology; Sansom, C., Markman, O., Eds.;
Scion Publishing Limited: 2007; Vol. 1.
(5) Hainrichson, M.; Nudelman, I.; Baasov, T. Org. Biomol. Chem.
2008, 6, 227.
(6) Demchenko, A. V. In Handbook of Chemical Glycosylation; Wiley-
VCH Verlag GmbH & Co. KGaA: 2008.
(7) Lemieux, R. U.; Nagabhushan, T. L.; O’Neill, I. K. Can. J. Chem.
1968, 46, 413.
(8) Schmidt, R. R.; Vankar, Y. D. Acc. Chem. Res. 2008, 41, 1059.
(9) Delaunay, T.; Poisson, T.; Jubault, P.; Pannecoucke, X. Eur. J. Org.
Chem. 2014, 2014, 7525.
(10) Xiang, S. H.; Ma, J. M.; Gorityala, B. K.; Liu, X. W. Carbohydr. Res.
2011, 346, 2957.
(11) Lorpitthaya, R.; Sophy, K. B.; Kuo, J. L.; Liu, X. W. Org. Biomol.
Chem. 2009, 7, 1284.
(12) Das, J.; Schmidt, R. R. Eur. J. Org. Chem. 1998, 1998, 1609.
(13) Winterfeld, G. A.; Schmidt, R. R. Angew. Chem., Int. Ed. 2001, 40,
2654.
(14) Winterfeld, G. A.; Khodair, A. I.; Schmidt, R. R. Eur. J. Org. Chem.
2003, 2003, 1009.
(15) Peng, P.; Geng, Y. Q.; Gottker-Schnetmann, I.; Schmidt, R. R.
(45) Tar
Eur. J. 2008, 14, 6078.
́ ́ ́ ́
kanyi, G.; Kiraly, P.; Varga, S.; Vakulya, B.; Soos, T. Chem. -
(46) Jang, H. B.; Rho, H. S.; Oh, J. S.; Nam, E. H.; Park, S. E.; Bae, H. Y.;
Song, C. E. Org. Biomol. Chem. 2010, 8, 3918.
(47) Nam, E. H.; Park, S. E.; Oh, J. S.; Some, S.; Kim, D. Y.; Bae, H. Y.;
Song, C. E. Bull. Korean Chem. Soc. 2011, 32, 3127.
(48) Lee, J. W.; Ryu, T. H.; Oh, J. S.; Bae, H. Y.; Bin Jang, H.; Song, C.
E. Chem. Commun. 2009, 41, 7224.
(49) Along with 6c, 35% of phenyl 2,3,4-tri-O-benzyl-α-D-
thioglucopyranoside S4 was also isolated. The reaction to yield 6d
also afforded 45% of oxazoline S5 derived from the acceptor. See the
(50) Nigudkar, S. S.; Demchenko, A. V. Chem. Sci. 2015, 6, 2687.
(51) Mayato, C.; Dorta, R. L.; Vazquez, J. T. Tetrahedron Lett. 2008, 49,
1396.
(52) Galan, M. C.; Corfield, A. P. Biochem. Soc. Trans. 2010, 38, 1368.
(53) Benito-Alifonso, D.; Jones, R. A.; Tran, A. T.; Woodward, H.;
Smith, N.; Galan, M. C. Beilstein J. Org. Chem. 2013, 9, 1867.
(54) Hollinger, M.; Abraha, F.; Oscarson, S. Carbohydr. Res. 2011, 346,
1454.
Org. Lett. 2015, 17, 1421.
(16) Xue, W. H.; Sun, J. S.; Yu, B. O. J. Org. Chem. 2009, 74, 5079.
(17) Medina, S.; Henderson, A. S.; Bower, J. F.; Galan, M. C. Chem.
Commun. 2015, 51, 8939.
(18) Balmond, E. I.; Benito-Alifonso, D.; Coe, D. M.; Alder, R. W.;
McGarrigle, E. M.; Galan, M. C. Angew. Chem., Int. Ed. 2014, 53, 8190.
(19) Balmond, E. I.; Galan, M. C.; McGarrigle, E. M. Synlett 2013, 24,
2335.
(20) Balmond, E. I.; Coe, D. M.; Galan, M. C.; McGarrigle, E. M.
Angew. Chem., Int. Ed. 2012, 51, 9152.
(21) Geng, Y. Q.; Kumar, A.; Faidallah, H. M.; Albar, H. A.; Mhkalid, I.
A.; Schmidt, R. R. Angew. Chem., Int. Ed. 2013, 52, 10089.
(22) Das, S.; Pekel, D.; Neudorfl, J. M.; Berkessel, A. Angew. Chem., Int.
Ed. 2015, 54, 12479.
(23) Medina, S.; Galan, M. C. Carbohydr. Chem. 2015, 41, 59.
(24) Cox, D. J.; Smith, M. D.; Fairbanks, A. J. Org. Lett. 2010, 12, 1452.
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