-
1
-
-
0001768006
-
-
K. C. Nicolaou, C. N. C. Boddy, S. Bräse, N. Winssinger, Angew. Chem. 1999, 111, 2230;
-
(1999)
Angew. Chem.
, vol.111
, pp. 2230
-
-
Nicolaou, K.C.1
Boddy, C.N.C.2
Bräse, S.3
Winssinger, N.4
-
5
-
-
0034632401
-
-
S. Boidnard, L. Neuville, M. Bois-Choussy, J. Zhu, Org. Lett. 2000, 2, 2459.
-
(2000)
Org. Lett.
, vol.2
, pp. 2459
-
-
Boidnard, S.1
Neuville, L.2
Bois-Choussy, M.3
Zhu, J.4
-
6
-
-
19944426067
-
-
E. A. Couladouros, E. N. Pitsinos, V. I. Moutsos, G. Sarakinos, Chem. Eur. J. 2005, 11, 406.
-
(2005)
Chem. Eur. J.
, vol.11
, pp. 406
-
-
Couladouros, E.A.1
Pitsinos, E.N.2
Moutsos, V.I.3
Sarakinos, G.4
-
7
-
-
33748565944
-
-
a) J. A. McRae, R. Y. Moir, J. J. Ursprung, H. H. Gibbs, J. Org. Chem. 1954, 19, 1500;
-
(1954)
J. Org. Chem.
, vol.19
, pp. 1500
-
-
McRae, J.A.1
Moir, R.Y.2
Ursprung, J.J.3
Gibbs, H.H.4
-
13
-
-
0032510279
-
-
K. Fuji, T. Oka, T. Kawabata, T. Kinoshita, Tetrahedron Lett. 1998, 39, 1373.
-
(1998)
Tetrahedron Lett.
, vol.39
, pp. 1373
-
-
Fuji, K.1
Oka, T.2
Kawabata, T.3
Kinoshita, T.4
-
18
-
-
0032492980
-
-
D. A. Evans, J. L. Katz, T. R. West, Tetrahedron Lett. 1998, 39, 2937;
-
(1998)
Tetrahedron Lett.
, vol.39
, pp. 2937
-
-
Evans, D.A.1
Katz, J.L.2
West, T.R.3
-
19
-
-
0032492942
-
-
D. M. T. Chan, K. L. Monaco, R. Wang, M. P. Winters, Tetrahedron Lett. 1998, 39, 2933;
-
(1998)
Tetrahedron Lett.
, vol.39
, pp. 2933
-
-
Chan, D.M.T.1
Monaco, K.L.2
Wang, R.3
Winters, M.P.4
-
22
-
-
33645237111
-
-
For the use of (-)-ephedrine-derived oxazolidines as protecting groups for aldehydes during lithiation, see: J. Clayden, Y. J. Y. Foricher, M. Helliwell, P. Johnson, D. Mitjans, V. Vinader, Org. Biomol. Chem. 2006, 4, 444.
-
(2006)
Org. Biomol. Chem.
, vol.4
, pp. 444
-
-
Clayden, J.1
Foricher, Y.J.Y.2
Helliwell, M.3
Johnson, P.4
Mitjans, D.5
Vinader, V.6
-
23
-
-
22244435422
-
-
(Eds.: Z. Rappoport, I. Marek), Wiley, Chichester
-
J. Clayden in Chemistry of Organolithium Compounds, Vol. 1 (Eds.: Z. Rappoport, I. Marek), Wiley, Chichester, 2004, p. 495;
-
(2004)
Chemistry of Organolithium Compounds, Vol. 1
, vol.1
, pp. 495
-
-
Clayden, J.1
-
26
-
-
33748536693
-
-
note
-
c value were simulated by using gNMR software (Adept Scientific).
-
-
-
-
27
-
-
33748573269
-
-
note
-
The half-lives are for the approach to the equilibrium mixture, not half-lives for bond rotation. The bond rotation monitored in 6c, 7c, and 8c does not in fact lead to interconversion of stereoisomers, but the half-life value is calculated in the same way for consistency.
-
-
-
-
28
-
-
0023198448
-
-
For examples in which trigonal substituents provide low barriers to bond rotation, see: A. I. Meyers, J. R. Flisak, R. A. Aitken, J. Am. Chem. Soc. 1987, 109, 5446;
-
(1987)
J. Am. Chem. Soc.
, vol.109
, pp. 5446
-
-
Meyers, A.I.1
Flisak, J.R.2
Aitken, R.A.3
-
29
-
-
0032558599
-
-
A. Ahmed, R. A. Bragg, J. Clayden, L. W. Lai, C. McCarthy, J. H. Pink, N. Westlund, S. A. Yasin, Tetrahedron 1998, 54, 13 277;
-
(1998)
Tetrahedron
, vol.54
, pp. 13277
-
-
Ahmed, A.1
Bragg, R.A.2
Clayden, J.3
Lai, L.W.4
McCarthy, C.5
Pink, J.H.6
Westlund, N.7
Yasin, S.A.8
-
32
-
-
0034684256
-
-
D. L. Boger, J.-H. Weng, S. Miyazaki, J. J. McAtee, S. L. Castle, S. H. Kim, Y. Mori, O. Rogel, H. Strittmatter, Q. Jin, J. Am. Chem. Soc. 2000, 122, 10 047.
-
(2000)
J. Am. Chem. Soc.
, vol.122
, pp. 10047
-
-
Boger, D.L.1
Weng, J.-H.2
Miyazaki, S.3
McAtee, J.J.4
Castle, S.L.5
Kim, S.H.6
Mori, Y.7
Rogel, O.8
Strittmatter, H.9
Jin, Q.10
-
34
-
-
33748548362
-
-
note
-
This estimation is made on the assumption that at least one pair of diastereotopic or more or less equally populated diastereoisomeric peaks would have a peak separation of > 0.1 ppm at the slow exchange limit.
-
-
-
-
35
-
-
33748535738
-
-
note
-
Substituents attached to the symmetrical ring may show coalescences at higher temperatures, which is indicative of much higher barriers, but these must be barriers to nonconcerted bond rotations; a full discussion will follow in a later report.
-
-
-
-
36
-
-
84986437005
-
-
F. Mohmadi, N. G. J. Richards, W. C. Guida, R. Liskamp, M. Lipton, C. Caufield, G. Chang, T. Hendrickson, W. C. Still, J. Comput. Chem. 1990, 11, 440.
-
(1990)
J. Comput. Chem.
, vol.11
, pp. 440
-
-
Mohmadi, F.1
Richards, N.G.J.2
Guida, W.C.3
Liskamp, R.4
Lipton, M.5
Caufield, C.6
Chang, G.7
Hendrickson, T.8
Still, W.C.9
-
38
-
-
49649157239
-
-
G. Montaudo, P. Finocchiaro, E. Trivellone, F. Bottino, P. Maravigna, Tetrahedron 1971, 27, 2125;
-
(1971)
Tetrahedron
, vol.27
, pp. 2125
-
-
Montaudo, G.1
Finocchiaro, P.2
Trivellone, E.3
Bottino, F.4
Maravigna, P.5
-
40
-
-
33748557211
-
-
note
-
Ground-state destabilization of tetra-ortho-substituted relative to tri-ortho-substituted diaryl ethers may also play a role in lowering the barrier, but the results presented in Table 1, entries 22-25 suggest that it is not an important one.
-
-
-
-
41
-
-
0000900061
-
-
For a discussion of geared rotation in related compounds, see: J. Clayden, J. H. Pink, Angew. Chem. 1998, 110, 2040;
-
(1998)
Angew. Chem.
, vol.110
, pp. 2040
-
-
Clayden, J.1
Pink, J.H.2
-
44
-
-
0037087637
-
-
R. A. Bragg, J. Clayden, G. A. Morris, J. H. Pink, Chem. Eur. J. 2002, 8, 1279;
-
(2002)
Chem. Eur. J.
, vol.8
, pp. 1279
-
-
Bragg, R.A.1
Clayden, J.2
Morris, G.A.3
Pink, J.H.4
-
45
-
-
18044376803
-
-
for a more general discussion of gearing effects, see: G. S. Kottas, L. I. Clarke, D. Horinek, J. Michl, Chem. Rev. 2005, 105, 1281;
-
(2005)
Chem. Rev.
, vol.105
, pp. 1281
-
-
Kottas, G.S.1
Clarke, L.I.2
Horinek, D.3
Michl, J.4
|