-
2
-
-
0033097654
-
-
Berecibar, A.; Grandjean, C; Siriwardena, A. Chem. Rev. 1999, 99, 779-844.
-
(1999)
Chem. Rev
, vol.99
, pp. 779-844
-
-
Berecibar, A.1
Grandjean, C.2
Siriwardena, A.3
-
7
-
-
0001745139
-
-
(d) Leblanc, Y.; Fitzsimmons, B. J.; Springer, J. P.; Rokach, J. J. Am. Chem. Soc. 1989, 111, 2995-3000.
-
(1989)
J. Am. Chem. Soc
, vol.111
, pp. 2995-3000
-
-
Leblanc, Y.1
Fitzsimmons, B.J.2
Springer, J.P.3
Rokach, J.4
-
9
-
-
0001995310
-
-
(f) Lafont, D.; Guilloux, P.; Descotes, G. Carbohydr Res. 1989, 193, 61-73.
-
(1989)
Carbohydr Res
, vol.193
, pp. 61-73
-
-
Lafont, D.1
Guilloux, P.2
Descotes, G.3
-
10
-
-
0030912722
-
-
(g) Du Bois, J.; Tomooka, C. S.; Hong, J.; Carreira, E. M. J. Am. Chem. Soc. 1997, 119, 3179-3180.
-
(1997)
J. Am. Chem. Soc
, vol.119
, pp. 3179-3180
-
-
Du Bois, J.1
Tomooka, C.S.2
Hong, J.3
Carreira, E.M.4
-
11
-
-
33750476666
-
-
(h) Guthikonda, K.; Wehn, P. M.; Caliando, B. J.; Du Bois, J. Tetrahedron 2006, 62, 11331-11342.
-
(2006)
Tetrahedron
, vol.62
, pp. 11331-11342
-
-
Guthikonda, K.1
Wehn, P.M.2
Caliando, B.J.3
Du Bois, J.4
-
13
-
-
0034598487
-
-
(b) Di Bussolo, V.; Liu, J.; Huffman, L. G., Jr.; Gin, D. Y. Angew. Chem., Int. Ed. 2000, 39, 204-207.
-
(2000)
Angew. Chem., Int. Ed
, vol.39
, pp. 204-207
-
-
Di Bussolo, V.1
Liu, J.2
Huffman Jr., L.G.3
Gin, D.Y.4
-
14
-
-
0037652302
-
-
(c) Liu, J.; Di Bussolo, V.; Gin, D. Y. Tetrahedron Lett 2003, 44, 4015-4018.
-
(2003)
Tetrahedron Lett
, vol.44
, pp. 4015-4018
-
-
Liu, J.1
Di Bussolo, V.2
Gin, D.Y.3
-
15
-
-
64349110403
-
-
For a strategy of internally directed glycal aminohydroxylation, see
-
For a strategy of internally directed glycal aminohydroxylation, see:
-
-
-
-
16
-
-
0034679468
-
-
(a) Nicolaou, K. C; Baran, P. S.; Zhong, Y.-L.; Vega, J. A. Angew. Chem., Int. Ed. 2000, 39, 2525-2529.
-
(2000)
Angew. Chem., Int. Ed
, vol.39
, pp. 2525-2529
-
-
Nicolaou, K.C.1
Baran, P.S.2
Zhong, Y.-L.3
Vega, J.A.4
-
17
-
-
0037070584
-
-
(b) Nicolaou, K. C; Baran, P. S.; Zhong, Y.-L.; Barluenga, S.; Hunt, K. W.; Kranich, R.; Vega, J. A. J. Am. Chem. Soc. 2002, 124, 2233-2244.
-
(2002)
J. Am. Chem. Soc
, vol.124
, pp. 2233-2244
-
-
Nicolaou, K.C.1
Baran, P.S.2
Zhong, Y.-L.3
Barluenga, S.4
Hunt, K.W.5
Kranich, R.6
Vega, J.A.7
-
18
-
-
0035825777
-
-
(a) Kan, C; Long, C. M.; Paul, M.; Ring, C. M.; Tully, S. E.; Rojas, C. M. Org. Lett. 2001, 3, 381-384.
-
(2001)
Org. Lett
, vol.3
, pp. 381-384
-
-
Kan, C.1
Long, C.M.2
Paul, M.3
Ring, C.M.4
Tully, S.E.5
Rojas, C.M.6
-
20
-
-
85044705488
-
-
Levites-Agababa, E.; Menhaji, E.; Perlson, L. N.; Rojas, C. M. Org. Lett. 2002, 4, 863-865.
-
(2002)
Org. Lett
, vol.4
, pp. 863-865
-
-
Levites-Agababa, E.1
Menhaji, E.2
Perlson, L.N.3
Rojas, C.M.4
-
21
-
-
18744398143
-
-
Bodner, R.; Marcellino, B. K.; Severino, A.; Smenton, A. L.; Rojas, C. M. J. Org. Chem. 2005, 70, 3988-3996.
-
(2005)
J. Org. Chem
, vol.70
, pp. 3988-3996
-
-
Bodner, R.1
Marcellino, B.K.2
Severino, A.3
Smenton, A.L.4
Rojas, C.M.5
-
22
-
-
0035793265
-
-
Espino, C. G.; Du Bois, J. Angew. Chem., Int. Ed. 2001, 40, 598-600.
-
(2001)
Angew. Chem., Int. Ed
, vol.40
, pp. 598-600
-
-
Espino, C.G.1
Du Bois, J.2
-
24
-
-
4644238043
-
-
(b) Padwa, A.; Flick, A. C; Leverett, C. A.; Stengel, T. J. Org. Chem. 2004, 69, 6377-6386.
-
(2004)
J. Org. Chem
, vol.69
, pp. 6377-6386
-
-
Padwa, A.1
Flick, A.C.2
Leverett, C.A.3
Stengel, T.4
-
25
-
-
64349104870
-
-
Related aziridinations
-
Related aziridinations:
-
-
-
-
26
-
-
0345791433
-
-
(a) Wehn, P. M.; Lee, J.; Du Bois, J. 2003, 5, 4823-4826.
-
(2003)
, vol.4823-4826
, Issue.5
-
-
Wehn, P.M.1
Lee, J.2
Du Bois, J.3
-
28
-
-
0001458273
-
-
(c) Duran, F.; Leman, L.; Ghini, A.; Burton, G.; Dauban, P.; Dodd, R. H. Org. Lett. 2002, 4, 2481-2483.
-
(2002)
Org. Lett
, vol.4
, pp. 2481-2483
-
-
Duran, F.1
Leman, L.2
Ghini, A.3
Burton, G.4
Dauban, P.5
Dodd, R.H.6
-
29
-
-
0037631116
-
-
(d) Liang, J.-L.; Yuan, S.-X.; Chan, P. W. H.; Che, C.-M. Tetrahedron Lett. 2003, 44, 5917-5920.
-
(2003)
Tetrahedron Lett
, vol.44
, pp. 5917-5920
-
-
Liang, J.-L.1
Yuan, S.-X.2
Chan, P.W.H.3
Che, C.-M.4
-
31
-
-
0037032268
-
-
(b) Donohoe, T. J.; Johnson, P. D.; Cowley, A.; Keenan, M. J Am. Chem. Soc. 2002, 124, 12934-12935.
-
(2002)
J Am. Chem. Soc
, vol.124
, pp. 12934-12935
-
-
Donohoe, T.J.1
Johnson, P.D.2
Cowley, A.3
Keenan, M.4
-
32
-
-
26844569944
-
-
(c) Lebel, H.; Huard, K.; Lectard, S. J. Am. Chem. Soc. 2005, 127, 14198-14199.
-
(2005)
J. Am. Chem. Soc
, vol.127
, pp. 14198-14199
-
-
Lebel, H.1
Huard, K.2
Lectard, S.3
-
35
-
-
0034794306
-
-
Dauban, P.; Saniére, L.; Tarrade, A.; Dodd, R. H. J. Am. Chem. Soc. 2001, 123, 7707-7708.
-
(2001)
J. Am. Chem. Soc
, vol.123
, pp. 7707-7708
-
-
Dauban, P.1
Saniére, L.2
Tarrade, A.3
Dodd, R.H.4
-
36
-
-
53849121623
-
-
Another Rh-nitrenoid approach to 2-amino glycosides, using glucal sulfamates: Lorpitthaya, R.; Xie, Z.-Z.; Kuo, J.-L.; Liu, X.-W. Chem. Eur. J. 2008, 14, 1561-1570.
-
Another Rh-nitrenoid approach to 2-amino glycosides, using glucal sulfamates: Lorpitthaya, R.; Xie, Z.-Z.; Kuo, J.-L.; Liu, X.-W. Chem. Eur. J. 2008, 14, 1561-1570.
-
-
-
-
37
-
-
0004288915
-
-
Hanessian, S, Ed, Marcel Dekker: New York
-
Fraser-Reid, B.; Madsen, R. In Preparative Carbohydrate Chemistry; Hanessian, S., Ed.; Marcel Dekker: New York, 1997; pp 339-356.
-
(1997)
Preparative Carbohydrate Chemistry
, pp. 339-356
-
-
Fraser-Reid, B.1
Madsen, R.2
-
39
-
-
64349111779
-
-
See Supporting Information for carbamate syntheses
-
See Supporting Information for carbamate syntheses.
-
-
-
-
40
-
-
84890760012
-
-
Evans, P. A, Ed, Wiley-VCH: Weinheim
-
(a) Espino, C. G.; Du Bois, J. In Modern Rhodium-Catalyzed Organic Reactions; Evans, P. A., Ed.; Wiley-VCH: Weinheim, 2005; pp 379-416.
-
(2005)
Modern Rhodium-Catalyzed Organic Reactions
, pp. 379-416
-
-
Espino, C.G.1
Du Bois, J.2
-
41
-
-
64349102612
-
-
See also footnote 17 of
-
See also footnote 17 of.
-
-
-
-
42
-
-
33646438818
-
-
(b) Kim, M.; Mulcahy, J. V.; Espino, C. G.; Du Bois, J. Org Lett. 2006, 8, 1073-1076.
-
(2006)
Org Lett
, vol.8
, pp. 1073-1076
-
-
Kim, M.1
Mulcahy, J.V.2
Espino, C.G.3
Du Bois, J.4
-
44
-
-
2542471780
-
-
Clark, J. S.; Dossetter, A. G.; Wong, Y.-S.; Townsend, R. J.; Whittingham, W. G.; Russell, C. A. J. Org. Chem. 2004, 69, 3886-3898.
-
(2004)
J. Org. Chem
, vol.69
, pp. 3886-3898
-
-
Clark, J.S.1
Dossetter, A.G.2
Wong, Y.-S.3
Townsend, R.J.4
Whittingham, W.G.5
Russell, C.A.6
-
45
-
-
84869264752
-
-
2 did not produce byproduct 8b (or any 7b) from 6b. We also noted earlier (ref 8) that tri-O-acetyl-D-glucal does not react under our conditions, though it is a substrate for Kirschning-type oxidation:
-
2 did not produce byproduct 8b (or any 7b) from 6b. We also noted earlier (ref 8) that tri-O-acetyl-D-glucal does not react under our conditions, though it is a substrate for Kirschning-type oxidation:
-
-
-
-
49
-
-
4544313955
-
-
Fiori, K. W.; Fleming, J. J.; Du Bois, J. Angew. Chem., Int. Ed. 2004, 43, 4349-4352.
-
(2004)
Angew. Chem., Int. Ed
, vol.43
, pp. 4349-4352
-
-
Fiori, K.W.1
Fleming, J.J.2
Du Bois, J.3
-
51
-
-
20444426203
-
-
(a) Toumieux, S.; Compain, P.; Martin, O. R. Tetrahedron Lett. 2005, 46, 4731-4735.
-
(2005)
Tetrahedron Lett
, vol.46
, pp. 4731-4735
-
-
Toumieux, S.1
Compain, P.2
Martin, O.R.3
-
52
-
-
33750090103
-
-
(b) Toumieux, S.; Compain, P.; Martin, O. R.; Selkti, M. Org. Lett. 2006, 8, 4493-4496.
-
(2006)
Org. Lett
, vol.8
, pp. 4493-4496
-
-
Toumieux, S.1
Compain, P.2
Martin, O.R.3
Selkti, M.4
-
54
-
-
0037148997
-
-
(b) Wardrop, D. J.; Zhang, W.; Fritz, J. Org Lett. 2002, 4, 489-492.
-
(2002)
Org Lett
, vol.4
, pp. 489-492
-
-
Wardrop, D.J.1
Zhang, W.2
Fritz, J.3
-
56
-
-
33750483259
-
-
An alternative would be catalyst-controlled chemoselectivity. In our systems, of various Rh(II) carboxylates examined, only Rh2(OAc) 4 and Du Bois's Rh2(esp)2 provided complete conversion, and neither catalyst was satisfactory in limiting C3-H oxidation. Catalyst control of chemoselectivity in rhodium nitrenoid and carbenoid insertions, respectively: (a) Hayes, C. J, Beavis, P. W, Humphries, L. A. Chem. Commun. 2006, 4501-4502
-
2 provided complete conversion, and neither catalyst was satisfactory in limiting C3-H oxidation. Catalyst control of chemoselectivity in rhodium nitrenoid and carbenoid insertions, respectively: (a) Hayes, C. J.; Beavis, P. W.; Humphries, L. A. Chem. Commun. 2006, 4501-4502.
-
-
-
-
57
-
-
36849038408
-
-
(b) Davies, H. M. L.; Coleman, M. G.; Ventura, D. L. Org. Lett. 2007, 9, 4971-4974.
-
(2007)
Org. Lett
, vol.9
, pp. 4971-4974
-
-
Davies, H.M.L.1
Coleman, M.G.2
Ventura, D.L.3
-
59
-
-
0030792114
-
-
(b) Roush, W. R.; Sebesta, D. P.; Bennett, C. E. Tetrahedron 1997, 53, 8825-8836.
-
(1997)
Tetrahedron
, vol.53
, pp. 8825-8836
-
-
Roush, W.R.1
Sebesta, D.P.2
Bennett, C.E.3
-
61
-
-
27844506623
-
-
Since dihydropyranones 8 are Michael acceptors for alcohols under basic or acidic conditions (for example: Mann, B.; Pitts, D.; Koviach, J. J. Carbohydr Chem 2005, 24, 161-168.), we verified their stability under the reaction conditions. See Supporting Information for details.
-
Since dihydropyranones 8 are Michael acceptors for alcohols under basic or acidic conditions (for example: Mann, B.; Pitts, D.; Koviach, J. J. Carbohydr Chem 2005, 24, 161-168.), we verified their stability under the reaction conditions. See Supporting Information for details.
-
-
-
-
62
-
-
85164065766
-
-
H4, H5 determinations.
-
H4, H5 determinations.
-
-
-
-
63
-
-
0000626637
-
-
van Roeckel, C. A. A.; Beetz, T.; van Aelst, S. F. Tetrahedron 1984, 40, 4097-4107.
-
(1984)
Tetrahedron
, vol.40
, pp. 4097-4107
-
-
van Roeckel, C.A.A.1
Beetz, T.2
van Aelst, S.F.3
-
64
-
-
38349004623
-
-
Liang, C; Collet, F.; Robert-Peillard, F.; Müller, P.; Dodd, R. H.; Dauban, P. J. Am. Chem. Soc. 2008, 130, 343-350.
-
(2008)
J. Am. Chem. Soc
, vol.130
, pp. 343-350
-
-
Liang, C.1
Collet, F.2
Robert-Peillard, F.3
Müller, P.4
Dodd, R.H.5
Dauban, P.6
-
65
-
-
0000892411
-
-
(a) Kita, Y.; Takada, T.; Gyoten, M.; Tohma, H.; Zenk, M. H.; Eichhorn, J. J. Org. Chem. 1996, 61, 5857-5864.
-
(1996)
J. Org. Chem
, vol.61
, pp. 5857-5864
-
-
Kita, Y.1
Takada, T.2
Gyoten, M.3
Tohma, H.4
Zenk, M.H.5
Eichhorn, J.6
-
66
-
-
33846919089
-
-
(b) Huang, X.; Shao, N.; Palani, A.; Aslanian, R. Tetrahedron Lett. 2007, 48, 1967-1971.
-
(2007)
Tetrahedron Lett
, vol.48
, pp. 1967-1971
-
-
Huang, X.1
Shao, N.2
Palani, A.3
Aslanian, R.4
|