-
15
-
-
0742269720
-
-
R.D. Crouch, C.A. Romany, A.C. Kreshock, K.A. Menconi, and J.L. Zile Tetrahedron Lett. 45 2004 1279
-
(2004)
Tetrahedron Lett.
, vol.45
, pp. 1279
-
-
Crouch, R.D.1
Romany, C.A.2
Kreshock, A.C.3
Menconi, K.A.4
Zile, J.L.5
-
18
-
-
0037201117
-
-
R.D. Crouch, J.M. Polizzi, R.A. Cleiman, C.J. Yi, and C.A. Romany Tetrahedron Lett. 43 2002 7151
-
(2002)
Tetrahedron Lett.
, vol.43
, pp. 7151
-
-
Crouch, R.D.1
Polizzi, J.M.2
Cleiman, R.A.3
Yi, C.J.4
Romany, C.A.5
-
19
-
-
0033574650
-
-
R.D. Crouch, M. Stieff, J.L. Frie, A.B. Cadwallader, and D.C. Bevis Tetrahedron Lett. 40 1999 3133
-
(1999)
Tetrahedron Lett.
, vol.40
, pp. 3133
-
-
Crouch, R.D.1
Stieff, M.2
Frie, J.L.3
Cadwallader, A.B.4
Bevis, D.C.5
-
20
-
-
0002874363
-
-
G. Bartoli, M. Bosco, E. Marcantoni, L. Sambri, and E. Torregiani Synlett 1998 209
-
(1998)
Synlett
, pp. 209
-
-
Bartoli, G.1
Bosco, M.2
Marcantoni, E.3
Sambri, L.4
Torregiani, E.5
-
24
-
-
0037182709
-
-
Y. Wu, J. Huang, X. Shen, C. Tang, and L. Li Org. Lett. 4 2002 2141
-
(2002)
Org. Lett.
, vol.4
, pp. 2141
-
-
Wu, Y.1
Huang, J.2
Shen, X.3
Tang, C.4
Li, L.5
-
28
-
-
1242338911
-
-
S. Kim, S.M. Jacobo, C.T. Chang, S. Bellone, W.S. Powell, and J. Rokach Tetrahedron Lett. 45 2004 1973
-
(2004)
Tetrahedron Lett.
, vol.45
, pp. 1973
-
-
Kim, S.1
Jacobo, S.M.2
Chang, C.T.3
Bellone, S.4
Powell, W.S.5
Rokach, J.6
-
29
-
-
0021260262
-
-
R.A. Olofson, J.T. Martz, J.-P. Senet, M. Piteau, and T. Malfroot J. Org Chem. 49 1984 2081
-
(1984)
J. Org Chem.
, vol.49
, pp. 2081
-
-
Olofson, R.A.1
Martz, J.T.2
Senet, J.-P.3
Piteau, M.4
Malfroot, T.5
-
31
-
-
37049068853
-
-
J.S. Davies, C.L. Higginbotham, E.J. Tremeer, C. Brown, and R.C. Treadgold J. Chem. Soc., Perkin. Trans. 1 1992 3043
-
(1992)
J. Chem. Soc., Perkin. Trans. 1
, pp. 3043
-
-
Davies, J.S.1
Higginbotham, C.L.2
Tremeer, E.J.3
Brown, C.4
Treadgold, R.C.5
-
33
-
-
28444476319
-
-
note
-
Determined from GC analysis using HP-5 column (Crosslinked 5% PH ME Polysiloxane).
-
-
-
-
34
-
-
28444468540
-
-
note
-
We examined the selective TES cleavage over TBDMS with lower amount of thionyl chloride (0.01, 0.02, 0.025 mol%), and the results were still less desirable than those obtained with 1-chloroethyl chloroformate (83-89% yield vs 93-95%, respectively).
-
-
-
-
35
-
-
28444460474
-
-
note
-
Per suggestion from one of the reviewers, commercially available 1.25 M HCl in methanol (Fluka) was examined in the desilylation. By employing varying amounts of HCl in methanol from 0.025, 0.05, 0.1, to 0.2 mol%, we obtained mono-desilylated alcohol (Table 1, 1 ) in 85, 89, 86, and 76% yields, respectively, along with diols. These yields were 8-21% lower than those obtained with CEC. When a very small amount (∼0.01 mol%) of methanolic HCl was employed, the yield of TES removal was less than 6%, and most starting material was recovered. We also carried out selective TBDMS removal over TIPS with 8a with varying amount of HCl, and yields were 73-83%, which are again lower than those obtained with CEC.
-
-
-
-
36
-
-
21544460203
-
-
For recent reports on successful application of in situ generated hydrogen halides to selective organic transformations, see: (a) C.-E. Yeom, S.Y. Lee, Y.J. Kim, and B.M. Kim Synlett 2005 1527
-
(2005)
Synlett
, pp. 1527
-
-
Yeom, C.-E.1
Lee, S.Y.2
Kim, Y.J.3
Kim, B.M.4
-
44
-
-
3042662232
-
-
Use of Pd/C at desilylation exhibited remarkable commercial supplier-dependent disparity. See: (a) T. Ikawa, H. Sajiki, and K. Hirota Tetrahedron 60 2004 6189
-
(2004)
Tetrahedron
, vol.60
, pp. 6189
-
-
Ikawa, T.1
Sajiki, H.2
Hirota, K.3
-
48
-
-
0000054361
-
-
Reports on chemoselective cleavage of aliphatic TES over phenolic one are rare and in case of TBDPS, only a few examples have been reported, see: (a) T. Oriyama, Y. Kobayashi, and K. Noda Synlett 1998 1047
-
(1998)
Synlett
, pp. 1047
-
-
Oriyama, T.1
Kobayashi, Y.2
Noda, K.3
-
55
-
-
0242330786
-
-
G.M. Mahandru, A.R.L. Skauge, S.K. Chowdhury, K.K.D. Amarasinghe, M.J. Heeg, and J. Montgomery J. Am. Chem. Soc. 125 2003 13481
-
(2003)
J. Am. Chem. Soc.
, vol.125
, pp. 13481
-
-
Mahandru, G.M.1
Skauge, A.R.L.2
Chowdhury, S.K.3
Amarasinghe, K.K.D.4
Heeg, M.J.5
Montgomery, J.6
-
61
-
-
0037182709
-
-
Y. Wu, J.-H. Huang, X. Shen, Q. Hu, C.-J. Tang, and L. Li Org. Lett. 4 2002 2141
-
(2002)
Org. Lett.
, vol.4
, pp. 2141
-
-
Wu, Y.1
Huang, J.-H.2
Shen, X.3
Hu, Q.4
Tang, C.-J.5
Li, L.6
-
77
-
-
0000062296
-
-
E. Alvarez, M.T. Díaz, R. Pérez, J.L. Ravelo, A. Regueiro, J.A. Vera, D. Zurita, and J.D. Martín J. Org. Chem. 59 1994 2848
-
(1994)
J. Org. Chem.
, vol.59
, pp. 2848
-
-
Alvarez, E.1
Díaz, M.T.2
Pérez, R.3
Ravelo, J.L.4
Regueiro, A.5
Vera, J.A.6
Zurita, D.7
Martín, J.D.8
-
78
-
-
1842503875
-
-
S. EI. Fangour, A. Guy, V. Despres, J.-P. Vidal, J.-C. Rossi, and T. Durand J. Org. Chem. 69 2004 2498
-
(2004)
J. Org. Chem.
, vol.69
, pp. 2498
-
-
Fangour, S.E.I.1
Guy, A.2
Despres, V.3
Vidal, J.-P.4
Rossi, J.-C.5
Durand, T.6
-
81
-
-
0037414541
-
-
T. Ishikawa, T. Mizuta, K. Hagiwara, T. Aikawa, T. Kudo, and S. Saito J. Org. Chem. 68 2003 3702
-
(2003)
J. Org. Chem.
, vol.68
, pp. 3702
-
-
Ishikawa, T.1
Mizuta, T.2
Hagiwara, K.3
Aikawa, T.4
Kudo, T.5
Saito, S.6
|