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Journal of Organic Chemistry

Volumn 79, Issue 23, 2014, Pages 11473-11482

Stereocontrolled O -glycosylation with palladium-catalyzed decarboxylative allylation

(4) Xiang, Shaohua a He, Jingxi a Tan, Yu Jia a Liu, Xue Wei a

a Nanyang Technological University (Singapore)

Author keywords

[No Author keywords available]

Indexed keywords

ADDITION REACTIONS; CARBOXYLATION; CATALYSIS; ESTERIFICATION;

ELECTRON-RICH; GLYCOSYL DONORS; NUCLEOPHILIC ADDITIONS; O-GLYCOSIDES; O-GLYCOSYLATION; PALLADIUM-CATALYZED; PALLADIUM-CATALYZED REACTIONS; PROTON ABSTRACTION;

GLYCOSYLATION;

ALCOHOL; CARBONIC ACID DERIVATIVE; GALACTOSE; GLUCOSE; GLYCOSIDE; MANNOSE; PALLADIUM; PROTON;

ADDITION REACTION; ALLYLATION; ARTICLE; CATALYSIS; CATALYST; DECARBOXYLATION; GLYCOSYLATION; ISOMER; NUCLEAR MAGNETIC RESONANCE; NUCLEOPHILICITY; PROTON NUCLEAR MAGNETIC RESONANCE; PROTON TRANSPORT; REACTION TIME; SYNTHESIS; TEMPERATURE;

EID: 84916211196 PISSN: 00223263 EISSN: 15206904 Source Type: Journal
DOI: 10.1021/jo502078c Document Type: Article

Times cited : (32)

References (67)

1
- 0028186224
- Schmidt, R. R.; Kinzy, W. Adv. Carbohydr. Chem. Biochem. 1994, 50, 21-123
- (1994) Adv. Carbohydr. Chem. Biochem. , vol.50 , pp. 21-123
- Schmidt, R.R.¹ Kinzy, W.²

2
- 0001094662
- Dwek, R. A. Chem. Rev. 1996, 96, 683-720
- (1996) Chem. Rev. , vol.96 , pp. 683-720
- Dwek, R.A.¹

3
- 0029739240
- Danishefsky, S. J.; Bilodeau, M. T. Angew. Chem., Int. Ed. 1996, 35, 1380-1419
- (1996) Angew. Chem., Int. Ed. , vol.35 , pp. 1380-1419
- Danishefsky, S.J.¹ Bilodeau, M.T.²

4
- 0035805264
- Nicolaou, K. C.; Mitchell, H. J. Angew. Chem., Int. Ed. 2001, 40, 1576-1624
- (2001) Angew. Chem., Int. Ed. , vol.40 , pp. 1576-1624
- Nicolaou, K.C.¹ Mitchell, H.J.²

5
- 0034698451
- Davis, B. G. J. J. Chem. Soc., Perkin Trans. 1 2000, 2137-2160
- (2000) J. Chem. Soc., Perkin Trans. 1 , pp. 2137-2160
- Davis, B.G.J.¹

6
- 0036026456
- Jensen, K. J. J. Chem. Soc., Perkin Trans. 1 2002, 2219-2233
- (2002) J. Chem. Soc., Perkin Trans. 1 , pp. 2219-2233
- Jensen, K.J.¹

7
- 33747036462
- Toshima, K. Carbohydr. Res. 2006, 341, 1282-1297
- (2006) Carbohydr. Res. , vol.341 , pp. 1282-1297
- Toshima, K.¹

8
- 34247853422
- Galonic, D. P.; Gin, D. Y. Nature 2007, 446, 1000-1008
- (2007) Nature , vol.446 , pp. 1000-1008
- Galonic, D.P.¹ Gin, D.Y.²

9
- 84890989536
- Wiley-VCH: Weinheim
- Demchenko, A. V. Handbook of Chemical Glycosylation; Wiley-VCH: Weinheim, 2008.
- (2008) Handbook of Chemical Glycosylation
- Demchenko, A.V.¹

10
- 0001823520
- Ferrier, R. J. J. Chem. Soc. C 1964, 5443-5449
- (1964) J. Chem. Soc. C , pp. 5443-5449
- Ferrier, R.J.¹

11
- 0001927976
- Ferrier, R. J.; Ciment, D. M. J. Chem. Soc. C 1966, 441-445
- (1966) J. Chem. Soc. C , pp. 441-445
- Ferrier, R.J.¹ Ciment, D.M.²

12
- 37049115004
- Ferrier, R. J.; Prasad, N. J. Chem. Soc., Chem. Commun. 1968, 476-477
- (1968) J. Chem. Soc., Chem. Commun. , pp. 476-477
- Ferrier, R.J.¹ Prasad, N.²

13
- 37049119941
- Ferrier, R. J.; Prasad, N. J. Chem. Soc. C 1969, 570-574
- (1969) J. Chem. Soc. C , pp. 570-574
- Ferrier, R.J.¹ Prasad, N.²

14
- 37049141139
- Ferrier, R. J.; Prasad, N. J. Chem. Soc. C 1969, 581-586
- (1969) J. Chem. Soc. C , pp. 581-586
- Ferrier, R.J.¹ Prasad, N.²

15
- 0032029798
- Bracherro, M. P.; Cabrera, E. F.; Gomez, G. M.; Peredes, L. M. R. Carbohydr. Res. 1998, 308, 181-190
- (1998) Carbohydr. Res. , vol.308 , pp. 181-190
- Bracherro, M.P.¹ Cabrera, E.F.² Gomez, G.M.³ Peredes, L.M.R.⁴

16
- 0035823432
- Murphy, P. V.; OBrien, J. L.; Smith, A. B., III Carbohydr. Res. 2001, 334, 327-335
- (2001) Carbohydr. Res. , vol.334 , pp. 327-335
- Murphy, P.V.¹ Obrien, J.L.² Smith, A.B.³

17
- 1642342224
- Babu, R. S.; ODoherty, G. A. J. Am. Chem. Soc. 2004, 126, 3428-3429
- (2004) J. Am. Chem. Soc. , vol.126 , pp. 3428-3429
- Babu, R.S.¹ Odoherty, G.A.²

18
- 33644797494
- Fakha, G.; Sinou, D. Molecules 2005, 10, 859-870
- (2005) Molecules , vol.10 , pp. 859-870
- Fakha, G.¹ Sinou, D.²

19
- 28244472379
- Hotha, S.; Tripathi, A. J. Comb. Chem. 2005, 7, 968-976
- (2005) J. Comb. Chem. , vol.7 , pp. 968-976
- Hotha, S.¹ Tripathi, A.²

20
- 27644525252
- Domon, D.; Fujiwara, K.; Ohtaniuchi, Y.; Takezawa, A.; Takeda, S.; Kawaski, H.; Murai, A.; Kawai, H.; Suzuki, T. Tetrahedron Lett. 2005, 46, 8279-8283
- (2005) Tetrahedron Lett. , vol.46 , pp. 8279-8283
- Domon, D.¹ Fujiwara, K.² Ohtaniuchi, Y.³ Takezawa, A.⁴ Takeda, S.⁵ Kawaski, H.⁶ Murai, A.⁷ Kawai, H.⁸ Suzuki, T.⁹

21
- 33645501568
- Tiwari, P.; Misra, A. K. J. Org. Chem. 2006, 71, 2911-2913
- (2006) J. Org. Chem. , vol.71 , pp. 2911-2913
- Tiwari, P.¹ Misra, A.K.²

22
- 33646439989
- Babu, R. S.; Guppi, S. R.; ODoherty, G. A. Org. Lett. 2006, 9, 1605-1608
- (2006) Org. Lett. , vol.9 , pp. 1605-1608
- Babu, R.S.¹ Guppi, S.R.² Odoherty, G.A.³

23
- 77953007988
- Guargna, A.; DAonzo, D.; Paolella, C.; Napolitano, C.; Palumbo, G. J. Org. Chem. 2010, 75, 3558-3568
- (2010) J. Org. Chem. , vol.75 , pp. 3558-3568
- Guargna, A.¹ Daonzo, D.² Paolella, C.³ Napolitano, C.⁴ Palumbo, G.⁵

24
- 84864245241
- Babu, R. S.; Chen, Q.; Kang, S.-W.; Zhou, M.; ODoherty, G. A. J. Am. Chem. Soc. 2012, 134, 11952-11955
- (2012) J. Am. Chem. Soc. , vol.134 , pp. 11952-11955
- Babu, R.S.¹ Chen, Q.² Kang, S.-W.³ Zhou, M.⁴ Odoherty, G.A.⁵

25
- 0000645983
- Ferrier, R. J. Top. Curr. Chem. 2001, 215, 153-175
- (2001) Top. Curr. Chem. , vol.215 , pp. 153-175
- Ferrier, R.J.¹

26
- 0347519078
- Ferrier, R. J.; Hoberg, J. O. Adv. Carbohydr. Chem. Biochem. 2003, 58, 55-119
- (2003) Adv. Carbohydr. Chem. Biochem. , vol.58 , pp. 55-119
- Ferrier, R.J.¹ Hoberg, J.O.²

27
- 0346600216
- Ferrier, R. J.; Zubkov, O. A. Org. React. 2003, 62, 569-736
- (2003) Org. React. , vol.62 , pp. 569-736
- Ferrier, R.J.¹ Zubkov, O.A.²

28
- 84887215836
- the references cited therein
- Gómez, A. M.; Lobo, F.; Uriel, C.; López, J. C. Eur. J. Org. Chem. 2013, 7221-7262 and the references cited therein
- (2013) Eur. J. Org. Chem. , pp. 7221-7262
- Gómez, A.M.¹ Lobo, F.² Uriel, C.³ López, J.C.⁴

29
- 84864624728
- McKay, M. J.; Nguyen, H. M. ACS Catal. 2012, 2, 1563-1595
- (2012) ACS Catal. , vol.2 , pp. 1563-1595
- McKay, M.J.¹ Nguyen, H.M.²

30
- 84863474047
- Li, X.; Zhu, J. J. Carbohydr. Chem. 2012, 31, 284-324
- (2012) J. Carbohydr. Chem. , vol.31 , pp. 284-324
- Li, X.¹ Zhu, J.²

31
- 0001247704
- Trost, B. M.; Gowland, F. W. J. Org. Chem. 1979, 44, 3448-3450
- (1979) J. Org. Chem. , vol.44 , pp. 3448-3450
- Trost, B.M.¹ Gowland, F.W.²

32
- 0000599127
- Dunkerton, L. V.; Serino, A. J. J. Org. Chem. 1982, 47, 2812-2184
- (1982) J. Org. Chem. , vol.47 , pp. 2812-2184
- Dunkerton, L.V.¹ Serino, A.J.²

33
- 0001322242
- RajanBabu, T. V. J. Org. Chem. 1985, 50, 3642-3644
- (1985) J. Org. Chem. , vol.50 , pp. 3642-3644
- Rajanbabu, T.V.¹

34
- 1042288189
- Kim, H.; Men, H.; Lee, C. J. Am. Chem. Soc. 2004, 126, 1336-1337
- (2004) J. Am. Chem. Soc. , vol.126 , pp. 1336-1337
- Kim, H.¹ Men, H.² Lee, C.³

35
- 34547962691
- Schuff, B. P.; Mercer, G. J.; Nguyen, H. M. Org. Lett. 2007, 9, 3173-3176
- (2007) Org. Lett. , vol.9 , pp. 3173-3176
- Schuff, B.P.¹ Mercer, G.J.² Nguyen, H.M.³

36
- 0037622656
- Comely, A. C.; Eelkema, R.; Minnaard, A. J.; Feringa, B. L. J. Am. Chem. Soc. 2003, 125, 8714-8715
- (2003) J. Am. Chem. Soc. , vol.125 , pp. 8714-8715
- Comely, A.C.¹ Eelkema, R.² Minnaard, A.J.³ Feringa, B.L.⁴

37
- 0141954268
- Babu, R. S.; ODoherty, G. A. J. Am. Chem. Soc. 2003, 125, 12406-12407
- (2003) J. Am. Chem. Soc. , vol.125 , pp. 12406-12407
- Babu, R.S.¹ Odoherty, G.A.²

38
- 79954581221
- Wang, H.-Y. L.; Rojanasakul, Y.; ODoherty, G. A. ACS Med. Chem. Lett. 2011, 2, 264-269
- (2011) ACS Med. Chem. Lett. , vol.2 , pp. 264-269
- Wang, H.-Y.L.¹ Rojanasakul, Y.² Odoherty, G.A.³

39
- 77955825189
- Torregrosa, R. R. P.; Ariyarathna, Y.; Chattopadhyay, K.; Tunge, J. A. J. Am. Chem. Soc. 2010, 132, 9280-9282
- (2010) J. Am. Chem. Soc. , vol.132 , pp. 9280-9282
- Torregrosa, R.R.P.¹ Ariyarathna, Y.² Chattopadhyay, K.³ Tunge, J.A.⁴

40
- 77956246870
- Weaver, J. D.; Ka, B. J.; Morris, D. K.; Thompson, W.; Tunge, J. A. J. Am. Chem. Soc. 2010, 132, 12179-12181
- (2010) J. Am. Chem. Soc. , vol.132 , pp. 12179-12181
- Weaver, J.D.¹ Ka, B.J.² Morris, D.K.³ Thompson, W.⁴ Tunge, J.A.⁵

41
- 79956111875
- Jana, R.; Partridge, J. J.; Tunge, J. A. Angew. Chem., Int. Ed. 2011, 50, 5157-5161
- (2011) Angew. Chem., Int. Ed. , vol.50 , pp. 5157-5161
- Jana, R.¹ Partridge, J.J.² Tunge, J.A.³

42
- 79952688980
- Weaver, J. D.; Recio, A.; Grenning, A. J.; Tunge, J. A. Chem. Rev. 2011, 111, 1846-1913
- (2011) Chem. Rev. , vol.111 , pp. 1846-1913
- Weaver, J.D.¹ Recio, A.² Grenning, A.J.³ Tunge, J.A.⁴

43
- 29044449348
- Trost, B. M.; Xu, J. J. Am. Chem. Soc. 2005, 127, 17180-12781
- (2005) J. Am. Chem. Soc. , vol.127 , pp. 17180-12781
- Trost, B.M.¹ Xu, J.²

44
- 33746191949
- Trost, B. M.; Bream, R. N.; Xu, J. Angew. Chem., Int. Ed. 2006, 45, 3109-3112
- (2006) Angew. Chem., Int. Ed. , vol.45 , pp. 3109-3112
- Trost, B.M.¹ Bream, R.N.² Xu, J.³

45
- 73249125403
- Trost, B. M.; Xu, J. Y.; Schmidt, T. J. Am. Chem. Soc. 2009, 131, 18343-18357
- (2009) J. Am. Chem. Soc. , vol.131 , pp. 18343-18357
- Trost, B.M.¹ Xu, J.Y.² Schmidt, T.³

46
- 79953234949
- Trost, B. M.; Schaffner, B.; Osipov, M.; Wilton, D. A. A. Angew. Chem., Int. Ed. 2011, 50, 3548-3551
- (2011) Angew. Chem., Int. Ed. , vol.50 , pp. 3548-3551
- Trost, B.M.¹ Schaffner, B.² Osipov, M.³ Wilton, D.A.A.⁴

47
- 9344253873
- Behenna, D. C.; Stoltz, B. M. J. Am. Chem. Soc. 2004, 126, 15044-15045
- (2004) J. Am. Chem. Soc. , vol.126 , pp. 15044-15045
- Behenna, D.C.¹ Stoltz, B.M.²

48
- 69549106158
- Sherden, N. H.; Behenna, D. C.; Virgil, S. C.; Stoltz, B. M. Angew. Chem., Int. Ed. 2009, 48, 6840-6843
- (2009) Angew. Chem., Int. Ed. , vol.48 , pp. 6840-6843
- Sherden, N.H.¹ Behenna, D.C.² Virgil, S.C.³ Stoltz, B.M.⁴

49
- 84863049058
- Behenna, D. C.; Liu, Y.; Yurino, T.; Kim, J.; White, D. E.; Virgil, S. C.; Stoltz, B. M. Nat. Chem. 2012, 4, 130-133
- (2012) Nat. Chem. , vol.4 , pp. 130-133
- Behenna, D.C.¹ Liu, Y.² Yurino, T.³ Kim, J.⁴ White, D.E.⁵ Virgil, S.C.⁶ Stoltz, B.M.⁷

50
- 27844517990
- Nakamura, M.; Hajra, A.; Endo, K.; Nakamura, E. Angew. Chem., Int. Ed. 2005, 44, 7248-7251
- (2005) Angew. Chem., Int. Ed. , vol.44 , pp. 7248-7251
- Nakamura, M.¹ Hajra, A.² Endo, K.³ Nakamura, E.⁴

51
- 33747879509
- You, S.-L.; Dai, L.-X. Angew. Chem., Int. Ed. 2006, 45, 5246-5248
- (2006) Angew. Chem., Int. Ed. , vol.45 , pp. 5246-5248
- You, S.-L.¹ Dai, L.-X.²

52
- 57249103677
- Kan, S. B. J.; Matsubara, R.; Berthiol, F.; Kobayashi, S. Chem. Commun. 2008, 6354-6356
- (2008) Chem. Commun. , pp. 6354-6356
- Kan, S.B.J.¹ Matsubara, R.² Berthiol, F.³ Kobayashi, S.⁴

53
- 58149197863
- Fields, W. H.; Khan, A. K.; Sabat, M.; Chruma, J. J. Org. Lett. 2008, 10, 5131-5134
- (2008) Org. Lett. , vol.10 , pp. 5131-5134
- Fields, W.H.¹ Khan, A.K.² Sabat, M.³ Chruma, J.J.⁴

54
- 84877703204
- Zeng, J.; Ma, J.; Xiang, S.; Cai, S.; Liu, X.-W. Angew. Chem., Int. Ed. 2013, 52, 5134-5137
- (2013) Angew. Chem., Int. Ed. , vol.52 , pp. 5134-5137
- Zeng, J.¹ Ma, J.² Xiang, S.³ Cai, S.⁴ Liu, X.-W.⁵

55
- 84887178936
- Xiang, S.; Lu, Z.; He, J.; Hoang, K. L. M.; Zeng, J.; Liu, X.-W. Chem.-Eur. J. 2013, 19, 14047-14051
- (2013) Chem.-Eur. J. , vol.19 , pp. 14047-14051
- Xiang, S.¹ Lu, Z.² He, J.³ Hoang, K.L.M.⁴ Zeng, J.⁵ Liu, X.-W.⁶

56
- 84896936227
- Xiang, S.; He, J.; Ma, J.; Liu, X.-W. Chem. Commun. 2014, 4222-4224
- (2014) Chem. Commun. , pp. 4222-4224
- Xiang, S.¹ He, J.² Ma, J.³ Liu, X.-W.⁴

57
- 0000282382
- Guibe, F. Tetrahedron Lett. 1981, 22, 3591-3594
- (1981) Tetrahedron Lett. , vol.22 , pp. 3591-3594
- Guibe, F.¹

58
- 0001147397
- Trost, B. M.; Runge, T. A. J. Am. Chem. Soc. 1981, 103, 7550-7559
- (1981) J. Am. Chem. Soc. , vol.103 , pp. 7550-7559
- Trost, B.M.¹ Runge, T.A.²

59
- 0000423379
- Tsuji, J.; Shimizu, I.; Minami, I.; Ohashi, Y. Tetrahedron lett. 1982, 23, 4809-4812
- (1982) Tetrahedron Lett. , vol.23 , pp. 4809-4812
- Tsuji, J.¹ Shimizu, I.² Minami, I.³ Ohashi, Y.⁴

60
- 33845379388
- Tsuji, J.; Shimizu, I.; Minami, I.; Ohashi, Y.; Sugiura, T.; Takahashi, K. J. Org. Chem. 1985, 50, 1523-1529
- (1985) J. Org. Chem. , vol.50 , pp. 1523-1529
- Tsuji, J.¹ Shimizu, I.² Minami, I.³ Ohashi, Y.⁴ Sugiura, T.⁵ Takahashi, K.⁶

61
- 0000213281
- Minami, I.; Shimizu, I.; Tsuji, J. J. Organomet. Chem. 1985, 296, 269-280
- (1985) J. Organomet. Chem. , vol.296 , pp. 269-280
- Minami, I.¹ Shimizu, I.² Tsuji, J.³

62
- 0029003845
- Knight, S. D.; Overman, L. E.; Pairaudeau, G. J. Am. Chem. Soc. 1995, 117, 5776-5788
- (1995) J. Am. Chem. Soc. , vol.117 , pp. 5776-5788
- Knight, S.D.¹ Overman, L.E.² Pairaudeau, G.³

63
- 0026262183
- Takai, I.; Ymamoto, A.; Ishido, V.; Sakakibara, T.; Yagi, E. Carbohydr. Res. 1991, 220, 195-207
- (1991) Carbohydr. Res. , vol.220 , pp. 195-207
- Takai, I.¹ Ymamoto, A.² Ishido, V.³ Sakakibara, T.⁴ Yagi, E.⁵

64
- 0026625920
- Booma, C.; Balasubramanian, K. K. Tetrahedron lett. 1992, 33, 3049-3052
- (1992) Tetrahedron Lett. , vol.33 , pp. 3049-3052
- Booma, C.¹ Balasubramanian, K.K.²

65
- 0028798770
- Ramesh, N. G.; Balasubramanian, K. K. Tetrahedron 1995, 51, 255-272
- (1995) Tetrahedron , vol.51 , pp. 255-272
- Ramesh, N.G.¹ Balasubramanian, K.K.²

66
- 68049114672
- Rawal, G. K.; Rani, S.; Kumari, N.; Vankar, Y. D. J. Org. Chem. 2009, 74, 5349-5355
- (2009) J. Org. Chem. , vol.74 , pp. 5349-5355
- Rawal, G.K.¹ Rani, S.² Kumari, N.³ Vankar, Y.D.⁴

67
- 0000388697
- Priebe, W.; Zamojski, A. Tetrahedron 1980, 36, 287-297
- (1980) Tetrahedron , vol.36 , pp. 287-297
- Priebe, W.¹ Zamojski, A.²

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