Borinic Acid Catalyzed Stereo- and Regioselective Couplings of Glycosyl Methanesulfonates

Journal of the American Chemical Society

Volumn 138, Issue 34, 2016, Pages 11058-11066

  D'Angelo, Kyan A ^a   Taylor, Mark S ^a  

^a UNIVERSITY OF TORONTO   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

CATALYSIS; CATALYSTS; COUPLINGS; REACTION RATES;

ASSOCIATIVE MECHANISMS; CATALYZED REACTIONS; EXCHANGE SPECTROSCOPIES; INTERCONVERSIONS; METHANESULFONATES; REACTION PROGRESS; REGIOSELECTIVE COUPLING; SITE SELECTIVITY;

CATALYST SELECTIVITY;

BORINIC ACID DERIVATIVE; DISACCHARIDE; MESYLIC ACID DERIVATIVE; MESYLIC ACID;

ARTICLE; CATALYST; CONTROLLED STUDY; GLYCOSYLATION; KINETICS; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PROCESS OPTIMIZATION; REGIOSELECTIVITY; ROOM TEMPERATURE; STEREOSELECTIVITY; CATALYSIS; CHEMISTRY; STEREOISOMERISM;

BORINIC ACIDS; CATALYSIS; GLYCOSYLATION; KINETICS; MESYLATES; STEREOISOMERISM;

EID: 84985031433     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/jacs.6b06943     Document Type: Article

References (81)

1. Crich, D.; Sun, S. J. Am. Chem. Soc. 1997, 119, 11217-11223 10.1021/ja971239r
2. Kim, J.-H.; Yang, H.; Park, J.; Boons, G.-J. J. Am. Chem. Soc. 2005, 127, 12090-12097 10.1021/ja052548h
3. Okada, Y.; Mukae, T.; Okajima, K.; Taira, M.; Fujita, M.; Yamada, H. Org. Lett. 2007, 9, 1573-1576 10.1021/ol070427b
4. Garcia, A.; Otte, D. A. L.; Salamant, W. A.; Sanzone, J. R.; Woerpel, K. A. Angew. Chem., Int. Ed. 2015, 54, 3061-3064 10.1002/anie.201410043
5. Kayastha, A. K.; Jia, X. G.; Yasomanee, J. P.; Demchenko, A. V. Org. Lett. 2015, 17, 4448-4451 10.1021/acs.orglett.5b02110
6. Augé, C.; Veyrières, A. J. Chem. Soc., Perkin Trans. 1 1979, 1825-1832 10.1039/P19790001825
7. Paulsen, H.; Hadamczyk, D.; Kutschker, W.; Bünsch, A. Liebigs Ann. Chem. 1985, 1985, 129-141 10.1002/jlac.198519850114
8. Cruzado, C.; Bernabe, M.; Martin-Lomas, M. Carbohydr. Res. 1990, 203, 296-301 10.1016/0008-6215(90)80028-2
9. Garregg, P. J.; Maloisel, J.-L.; Oscarson, S. Synthesis 1995, 1995, 409-414 10.1055/s-1995-3918
10. Oshima, K.; Aoyama, Y. J. Am. Chem. Soc. 1999, 121, 2315-2316 10.1021/ja982395g
11. Kaji, E.; Harita, N. Tetrahedron Lett. 2000, 41, 53-56 10.1016/S0040-4039(99)01997-8
12. Kaji, E.; Shibayama, K.; In, K. Tetrahedron Lett. 2003, 44, 4881-4885 10.1016/S0040-4039(03)01095-5
13. Wu, B.; Li, M.; O'Doherty, G. A. Org. Lett. 2010, 12, 5466-5469 10.1021/ol1023344
14. Maggi, A.; Madsen, R. Eur. J. Org. Chem. 2013, 2013, 2683-2691 10.1002/ejoc.201300026
15. Pelletier, G.; Zwicker, A.; Allen, C. L.; Schepartz, A.; Miller, S. J. J. Am. Chem. Soc. 2016, 138, 3175-3182 10.1021/jacs.5b13384
16. Gouliaras, C.; Lee, D.; Chan, L.; Taylor, M. S. J. Am. Chem. Soc. 2011, 133, 13926-13929 10.1021/ja2062715
17. Muramatsu, W.; Yoshimatsu, H. Adv. Synth. Catal. 2013, 355, 2518-2524 10.1002/adsc.201300414
18. Bajaj, S. O.; Sharif, E. U.; Akhmedov, N. G.; O'Doherty, G. A. Chem. Sci. 2014, 5, 2230-2234 10.1039/c4sc00593g
19. Mulani, S. K.; Hung, W.-C.; Ingle, A. B.; Shiau, K.-S.; Mong, K.-K. T. Org. Biomol. Chem. 2014, 12, 1184-1197 and references cited therein 10.1039/c3ob42129e
20. Mukaiyama, T.; Matsubara, K. Chem. Lett. 1992, 21, 1041-1044 10.1246/cl.1992.1041
21. Fukase, K.; Hasuoka, A.; Kinoshita, I.; Aoki, Y.; Kusumoto, S. Tetrahedron 1995, 51, 4923-4932 10.1016/0040-4020(95)98690-J
22. Lemieux, R. U.; Hendricks, K. B.; Stick, R. V.; James, K. J. Am. Chem. Soc. 1975, 97, 4056-4062 10.1021/ja00847a032
23. Reisman, S. E.; Doyle, A. G.; Jacobsen, E. N. J. Am. Chem. Soc. 2008, 130, 7198-7199 10.1021/ja801514m
24. Mensah, E. A.; Nguyen, H. M. J. Am. Chem. Soc. 2009, 131, 8778-8780 10.1021/ja903123b
25. Cox, D. J.; Smith, M. D.; Fairbanks, A. J. Org. Lett. 2010, 12, 1452-1455 10.1021/ol1001895
26. Geng, Y.; Kumar, A.; Faidallah, H. M.; Albar, H. A.; Mhkalid, I. A.; Schmidt, R. R. Angew. Chem., Int. Ed. 2013, 52, 10089-10092 10.1002/anie.201302158
27. Beale, T. M.; Moon, P. J.; Taylor, M. S. Org. Lett. 2014, 16, 3604-3607 10.1021/ol501711v
28. Peng, P.; Schmidt, R. R. J. Am. Chem. Soc. 2015, 137, 12653-12659 10.1021/jacs.5b07895
29. Tanaka, M.; Nashida, J.; Takahashi, D.; Toshima, K. Org. Lett. 2016, 18, 2288-2291 10.1021/acs.orglett.6b00926
30. Breton, C.; Snajdrová, L.; Jeanneau, C.; Koca, J.; Imberty, A. Glycobiology 2006, 16, 29-37R
31. Hancock, S. M.; Vaughan, M. D.; Withers, S. G. Curr. Opin. Chem. Biol. 2006, 10, 509-519 10.1016/j.cbpa.2006.07.015
32. Schmaltz, R. M.; Hanson, S. R.; Wong, C.-H. Chem. Rev. 2011, 111, 4259-4307 10.1021/cr200113w
33. Beale, T. M.; Taylor, M. S. Org. Lett. 2013, 15, 1358-1361 10.1021/ol4003042
34. Mancini, R. S.; McClary, C. A.; Anthonipillai, S.; Taylor, M. S. J. Org. Chem. 2015, 80, 8501-8510 10.1021/acs.joc.5b00950
35. Li, S.-P.; Hsiao, W.-C.; Yu, C.-C.; Chien, W.-T.; Lin, H.-J.; Huang, L.-D.; Lin, C.-H.; Wu, W.-L.; Wu, S.-H.; Lin, C.-C. Adv. Synth. Catal. 2014, 356, 3199-3213 10.1002/adsc.201400066
36. Mootoo, D. R.; Konradsson, P.; Ududong, U.; Fraser-Reid, B. J. Am. Chem. Soc. 1988, 110, 5583-5584 10.1021/ja00224a060
37. Kronzer, F. J.; Schuerch, C. Carbohydr. Res. 1973, 27, 379-390 10.1016/S0008-6215(00)81320-8
38. Eby, R.; Schuerch, C. Carbohydr. Res. 1974, 34, 79-90 10.1016/S0008-6215(00)80372-9
39. Machinami, T.; Suami, T. Chem. Lett. 1974, 1177-1180 10.1246/cl.1974.1177
40. Koto, S.; Hamada, Y.; Zen, S. Chem. Lett. 1975, 587-588 10.1246/cl.1975.587
41. Leroux, J.; Perlin, A. S. Carbohydr. Res. 1978, 67, 163-178 10.1016/S0008-6215(00)83739-8
42. Koto, S.; Sato, T.; Morishima, N.; Zen, S. Bull. Chem. Soc. Jpn. 1980, 53, 1761-1762 10.1246/bcsj.53.1761
43. Srivastava, V. K.; Schuerch, C. J. Org. Chem. 1981, 46, 1121-1126 10.1021/jo00319a016
44. Szeja, W. Synthesis 1988, 1988, 223-224 10.1055/s-1988-27519
45. Lee, D.; Williamson, C. L.; Chan, L.; Taylor, M. S. J. Am. Chem. Soc. 2012, 134, 8260-8267 10.1021/ja302549c
46. Garcia, B. A.; Poole, J. L.; Gin, D. Y. J. Am. Chem. Soc. 1997, 119, 7597-7598 10.1021/ja971067y
47. Nguyen, H. M.; Chen, Y.; Duron, S. G.; Gin, D. Y. J. Am. Chem. Soc. 2001, 123, 8766-8772 10.1021/ja015968p
48. Crich, D.; Smith, M. J. Am. Chem. Soc. 2001, 123, 9015-9020 10.1021/ja0111481
49. Nokami, T.; Shibuya, A.; Tsuyama, H.; Suga, S.; Bowers, A. A.; Crich, D.; Yoshida, J.-i. J. Am. Chem. Soc. 2007, 129, 10922-10928 10.1021/ja072440x
50. Crich, D. J. Carbohydr. Chem. 2002, 21, 663-686 10.1081/CAR-120016486
51. Crich, D. Acc. Chem. Res. 2010, 43, 1144-1153 10.1021/ar100035r
52. Frihed, T. G.; Bols, M.; Pedersen, C. M. Chem. Rev. 2015, 115, 4963-5013 10.1021/cr500434x
53. Boebel, T. A.; Gin, D. Y. Angew. Chem., Int. Ed. 2003, 42, 5874-5877 10.1002/anie.200352761
54. Boebel, T. A.; Gin, D. Y. J. Org. Chem. 2005, 70, 5818-5826 10.1021/jo050294c
55. Issa, J. P.; Steliotes, E.; Bennett, C. S. Org. Lett. 2013, 15, 4170-4173 10.1021/ol4018547
56. Issa, J. P.; Bennett, C. S. J. Am. Chem. Soc. 2014, 136, 5740-5744 10.1021/ja500410c
57. Truce, W. E.; Campbell, R. W. J. Am. Chem. Soc. 1966, 88, 3599-3604 10.1021/ja00967a024
58. Dimitrijević, E.; Taylor, M. S. Chem. Sci. 2013, 4, 3298-3303 10.1039/c3sc51172c
59. Crich, D.; de la Mora, M.; Vinod, A. U. J. Org. Chem. 2003, 68, 8142-8148 10.1021/jo0349882
60. Islam, M.; Gayatri, G.; Hotha, S. J. Org. Chem. 2015, 80, 7937-7945 10.1021/acs.joc.5b00964
61. Perrin, C. L.; Dwyer, T. J. Chem. Rev. 1990, 90, 935-967 10.1021/cr00104a002
62. Kumar, A.; Wagner, G.; Ernst, R. R.; Wuethrich, K. J. Am. Chem. Soc. 1981, 103, 3654-3658 10.1021/ja00403a008
63. Haindl, M. H.; Hioe, J.; Gschwind, R. J. Am. Chem. Soc. 2015, 137, 12835-12842 10.1021/jacs.5b03420
64. Horenstein, N. A. Adv. Phys. Org. Chem. 2006, 41, 275-314 10.1016/S0065-3160(06)41005-4
65. Crich, D. J. Org. Chem. 2011, 76, 9193-9209 10.1021/jo2017026
66. Krumper, J. R.; Salamant, W. A.; Woerpel, K. A. Org. Lett. 2008, 10, 4907-4910 10.1021/ol8019956
67. Wurst, J. M.; Liu, G.; Tan, D. S. J. Am. Chem. Soc. 2011, 133, 7916-7925 10.1021/ja201249c
68. Huang, M.; Garrett, G. E.; Birlirakis, N.; Bohé, L.; Pratt, D. A.; Crich, D. Nat. Chem. 2012, 4, 663-667 10.1038/nchem.1404
69. Chan, J.; Tang, A.; Bennet, A. J. J. Am. Chem. Soc. 2012, 134, 1212-1220 10.1021/ja209339j
70. Huang, M.; Retailleau, P.; Bohé, L.; Crich, D. J. Am. Chem. Soc. 2012, 134, 14746-14749 10.1021/ja307266n
71. Chan, J.; Sannikova, N.; Tang, A.; Bennet, A. J. J. Am. Chem. Soc. 2014, 136, 12225-12228 10.1021/ja506092h
72. Bohé, L.; Crich, D. Carbohydr. Res. 2015, 403, 48-59 10.1016/j.carres.2014.06.020
73. Wulff, G.; Röhle, G. Chem. Ber. 1972, 105, 1122-1132 10.1002/cber.19721050405
74. Bowden, T.; Garegg, P. J.; Maloisel, J.-L.; Konradsson, P. Isr. J. Chem. 2001, 40, 271-277 10.1560/P2J6-2MN2-0WHQ-R3BF
75. Fang, T.; Gu, Y.; Huang, W.; Boons, G.-J. J. Am. Chem. Soc. 2016, 138, 3002-3011 10.1021/jacs.5b08436
76. Blackmond, D. G. Angew. Chem., Int. Ed. 2005, 44, 4302-4320 10.1002/anie.200462544
77. Blackmond, D. G. J. Am. Chem. Soc. 2015, 137, 10852-10866 10.1021/jacs.5b05841
78. Bateman, L. C.; Church, M. G.; Hughes, E. D.; Ingold, C. K.; Taher, N. A. J. Chem. Soc. 1940, 979-1011 10.1039/jr9400000979
79. Kubo, Y.; Kobayashi, A.; Ishida, T.; Misawa, Y.; James, T. D. Chem. Commun. 2005, 2846-2848 10.1039/b503588k
80. Wan, W.-M.; Chen, F.; Jäkle, F. Angew. Chem., Int. Ed. 2014, 53, 8934-8938 10.1002/anie.201403703
81. Mártinez-Aguirre, M. A.; Yatsimirsky, A. K. J. Org. Chem. 2015, 80, 4985-4993 10.1021/acs.joc.5b00377