-
1
-
-
0037201534
-
-
For a recent review, see: M. Liu, M. P. Sibi, Tetrahedron 2002, 58, 7991; see also: E. Juaristi, H. Lopez-Ruiz, Curr. Med. Chem. 1999, 6, 983.
-
(2002)
Tetrahedron
, vol.58
, pp. 7991
-
-
Liu, M.1
Sibi, M.P.2
-
2
-
-
0345151817
-
-
For a recent review, see: M. Liu, M. P. Sibi, Tetrahedron 2002, 58, 7991; see also: E. Juaristi, H. Lopez-Ruiz, Curr. Med. Chem. 1999, 6, 983.
-
(1999)
Curr. Med. Chem.
, vol.6
, pp. 983
-
-
Juaristi, E.1
Lopez-Ruiz, H.2
-
3
-
-
2942514165
-
-
For selected recent examples, see: a) W. Tang, W. Wang, Y. Chi, X. Zhang, Angew. Chem. 2003, 115, 973; Angew. Chem. Int. Ed. 2003, 42, 3509;
-
(2003)
Angew. Chem.
, vol.115
, pp. 973
-
-
Tang, W.1
Wang, W.2
Chi, Y.3
Zhang, X.4
-
4
-
-
0042531839
-
-
For selected recent examples, see: a) W. Tang, W. Wang, Y. Chi, X. Zhang, Angew. Chem. 2003, 115, 973; Angew. Chem. Int. Ed. 2003, 42, 3509;
-
(2003)
Angew. Chem. Int. Ed.
, vol.42
, pp. 3509
-
-
-
5
-
-
0042626473
-
-
b) W. Tang, S. Wu, X. Zhang, J. Am. Chem. Soc. 2003, 125, 9570;
-
(2003)
J. Am. Chem. Soc.
, vol.125
, pp. 9570
-
-
Tang, W.1
Wu, S.2
Zhang, X.3
-
6
-
-
0034734313
-
-
c) H. Ishitani, M. Ueno, S. Kobayashi, J. Am. Chem. Soc. 2000, 122, 8280;
-
(2000)
J. Am. Chem. Soc.
, vol.122
, pp. 8280
-
-
Ishitani, H.1
Ueno, M.2
Kobayashi, S.3
-
9
-
-
0032496927
-
-
f) M. P. Sibi, J. J. Shay, M. Liu, C. P. Jasperse, J. Am. Chem. Soc. 1998, 120, 6615;
-
(1998)
J. Am. Chem. Soc.
, vol.120
, pp. 6615
-
-
Sibi, M.P.1
Shay, J.J.2
Liu, M.3
Jasperse, C.P.4
-
10
-
-
0141732263
-
-
g) M. P. Sibi, N. Prabagaran, S. G. Ghorpade, C. P. Jasperse, J. Am. Chem. Soc. 2003, 125, 11796.
-
(2003)
J. Am. Chem. Soc.
, vol.125
, pp. 11796
-
-
Sibi, M.P.1
Prabagaran, N.2
Ghorpade, S.G.3
Jasperse, C.P.4
-
11
-
-
0038688047
-
-
a) H. M. L. Davies, C. Venkataramani, Angew. Chem. 2002, 114, 2301; Angew. Chem. Int. Ed. 2002, 41, 2197;
-
(2002)
Angew. Chem.
, vol.114
, pp. 2301
-
-
Davies, H.M.L.1
Venkataramani, C.2
-
12
-
-
0037124920
-
-
a) H. M. L. Davies, C. Venkataramani, Angew. Chem. 2002, 114, 2301; Angew. Chem. Int. Ed. 2002, 41, 2197;
-
(2002)
Angew. Chem. Int. Ed.
, vol.41
, pp. 2197
-
-
-
13
-
-
0037449670
-
-
b) U. Eilitz, F. Leßmann, O. Seidelmann, V. Wendisch, Tetrahedron: Asymmetry 2003, 14, 189;
-
(2003)
Tetrahedron: Asymmetry
, vol.14
, pp. 189
-
-
Eilitz, U.1
Leßmann, F.2
Seidelmann, O.3
Wendisch, V.4
-
14
-
-
0037414323
-
-
c) A. Duursma, A. J. Minnaard, B. L. Feringa, J. Am. Chem. Soc. 2003, 125, 3700;
-
(2003)
J. Am. Chem. Soc.
, vol.125
, pp. 3700
-
-
Duursma, A.1
Minnaard, A.J.2
Feringa, B.L.3
-
16
-
-
0242515860
-
-
e) H.-S. Lee, J.-S. Park, B. M. Kim, S. H. Gellman, J. Org. Chem. 2003, 68, 1575;
-
(2003)
J. Org. Chem.
, vol.68
, pp. 1575
-
-
Lee, H.-S.1
Park, J.-S.2
Kim, B.M.3
Gellman, S.H.4
-
17
-
-
0042305011
-
-
f) D. Seebach, L. Schaeffer, F. Gessier, P. Bindschädler, C. Jäger, D. Josien, S. Kopp, G. Lelais, Y. R. Mahajan, P. Micuch, R. Sebesta, B. W. Schweizer, Helv. Chim. Acta 2003, 86, 1852.
-
(2003)
Helv. Chim. Acta
, vol.86
, pp. 1852
-
-
Seebach, D.1
Schaeffer, L.2
Gessier, F.3
Bindschädler, P.4
Jäger, C.5
Josien, D.6
Kopp, S.7
Lelais, G.8
Mahajan, Y.R.9
Micuch, P.10
Sebesta, R.11
Schweizer, B.W.12
-
18
-
-
0030903772
-
-
Cryptophycins: a) G. V. Subbaraju, T. Golakoti, G. M. L. Patterson, R. E. Moore, J. Nat. Prod. 1997, 60, 302;
-
(1997)
J. Nat. Prod.
, vol.60
, pp. 302
-
-
Subbaraju, G.V.1
Golakoti, T.2
Patterson, G.M.L.3
Moore, R.E.4
-
19
-
-
0032881267
-
-
biologically active β-peptides: b) M. Werder, H. Hausre, S. Abele, D. Seebach, Helv. Chim. Acta 1999, 82, 1774.
-
(1999)
Helv. Chim. Acta
, vol.82
, pp. 1774
-
-
Werder, M.1
Hausre, H.2
Abele, S.3
Seebach, D.4
-
20
-
-
0041878683
-
-
For recent reviews on enantioselective radical processes, see: a) M. P. Sibi, S. Manyem, J. Zimmerman, Chem. Rev. 2003, 103, 3263; M. P. Sibi, N. A. Porter, Acc. Chem. Res. 1999, 32, 163;
-
(2003)
Chem. Rev.
, vol.103
, pp. 3263
-
-
Sibi, M.P.1
Manyem, S.2
Zimmerman, J.3
-
21
-
-
0032960346
-
-
For recent reviews on enantioselective radical processes, see: a) M. P. Sibi, S. Manyem, J. Zimmerman, Chem. Rev. 2003, 103, 3263; M. P. Sibi, N. A. Porter, Acc. Chem. Res. 1999, 32, 163;
-
(1999)
Acc. Chem. Res.
, vol.32
, pp. 163
-
-
Sibi, M.P.1
Porter, N.A.2
-
22
-
-
0033588317
-
-
for examples of H-atom transfer mediated by chiral Lewis acids, see: b) M. Murakata, H. Tsutsui, N. Takeuchi, O. Hoshino, Tetrahedron 1999, 55, 10295;
-
(1999)
Tetrahedron
, vol.55
, pp. 10295
-
-
Murakata, M.1
Tsutsui, H.2
Takeuchi, N.3
Hoshino, O.4
-
23
-
-
0000350102
-
-
c) H. Urabe, K. Yamashita, K. Suzuki, K. Kobayashi, F. Sato, J. Org. Chem. 1995, 60, 3576;
-
(1995)
J. Org. Chem.
, vol.60
, pp. 3576
-
-
Urabe, H.1
Yamashita, K.2
Suzuki, K.3
Kobayashi, K.4
Sato, F.5
-
24
-
-
0000784209
-
-
d) M. P. Sibi, Y. Asano, J. B. Sausker, Angew. Chem. 2001, 113, 1333; Angew. Chem. Int. Ed. 2091, 40, 1293;
-
(2001)
Angew. Chem.
, vol.113
, pp. 1333
-
-
Sibi, M.P.1
Asano, Y.2
Sausker, J.B.3
-
25
-
-
4544351094
-
-
d) M. P. Sibi, Y. Asano, J. B. Sausker, Angew. Chem. 2001, 113, 1333; Angew. Chem. Int. Ed. 2091, 40, 1293;
-
(2091)
Angew. Chem. Int. Ed.
, vol.40
, pp. 1293
-
-
-
27
-
-
0005466990
-
-
for selected examples of enantioselective reductions with chiral H-atom transfer reagents, see: f) M. Blumenstein, K. Schwarzkopf, J. O. Metzger, Angew. Chem. 1997, 109, 245; Angew. Chem. Int. Ed. Engl. 1997, 36, 235;
-
(1997)
Angew. Chem.
, vol.109
, pp. 245
-
-
Blumenstein, M.1
Schwarzkopf, K.2
Metzger, J.O.3
-
28
-
-
0030935083
-
-
for selected examples of enantioselective reductions with chiral H-atom transfer reagents, see: f) M. Blumenstein, K. Schwarzkopf, J. O. Metzger, Angew. Chem. 1997, 109, 245; Angew. Chem. Int. Ed. Engl. 1997, 36, 235;
-
(1997)
Angew. Chem. Int. Ed. Engl.
, vol.36
, pp. 235
-
-
-
29
-
-
0034868562
-
-
g) C. H. Schiesser, M. A. Skidmore, J. M. White, Aust. J. Chem. 2001, 54, 199;
-
(2001)
Aust. J. Chem.
, vol.54
, pp. 199
-
-
Schiesser, C.H.1
Skidmore, M.A.2
White, J.M.3
-
31
-
-
0033533520
-
-
i) D. Dakternieks, K. Dunn, V. T. Perchyonok, C. H. Schiesser, Chem. Commun. 1999, 1665;
-
(1999)
Chem. Commun.
, pp. 1665
-
-
Dakternieks, D.1
Dunn, K.2
Perchyonok, V.T.3
Schiesser, C.H.4
-
32
-
-
0004269715
-
-
(Eds.: P. Renaud, M. P. Sibi), Wiley-VCH, Weinheim
-
j) for general information on radical reactions, see: Radicals in Organic Synthesis (Eds.: P. Renaud, M. P. Sibi), Wiley-VCH, Weinheim, 2001.
-
(2001)
Radicals in Organic Synthesis
-
-
-
35
-
-
0034694704
-
-
For reports on seven- and eight-membered metal chelates in stereoselective radical reactions, see: a) A. Hayen, R. Koch, W. Saak, D. Haase, J. Metzger, J. Am. Chem. Soc. 2000, 122, 12458;
-
(2000)
J. Am. Chem. Soc.
, vol.122
, pp. 12458
-
-
Hayen, A.1
Koch, R.2
Saak, W.3
Haase, D.4
Metzger, J.5
-
36
-
-
0000502433
-
-
b) A. Hayen, R. Koch, J. O. Metzger, Angew. Chem. 2000, 112, 2898; Angew. Chem. Int. Ed. 2000, 39, 2758;
-
(2000)
Angew. Chem.
, vol.112
, pp. 2898
-
-
Hayen, A.1
Koch, R.2
Metzger, J.O.3
-
37
-
-
0034604591
-
-
b) A. Hayen, R. Koch, J. O. Metzger, Angew. Chem. 2000, 112, 2898; Angew. Chem. Int. Ed. 2000, 39, 2758;
-
(2000)
Angew. Chem. Int. Ed.
, vol.39
, pp. 2758
-
-
-
38
-
-
0038741725
-
-
c) H. Nagano, H. Ohkouchi, T. Yajima, Tetrahedron 2003, 59, 3649;
-
(2003)
Tetrahedron
, vol.59
, pp. 3649
-
-
Nagano, H.1
Ohkouchi, H.2
Yajima, T.3
-
40
-
-
0034853422
-
-
For a report on radical additions to acrylates leading to racemic products, see: J. Huck, J.-M. Receveur, M.-L. Roumestant, J. Martinez, Synlett 2001, 1467.
-
(2001)
Synlett
, pp. 1467
-
-
Huck, J.1
Receveur, J.-M.2
Roumestant, M.-L.3
Martinez, J.4
-
41
-
-
0034026611
-
-
For the synthesis of substrates and details on experimental conditions, see the Supporting Information and D. Basavaiah, M. Krishnamacharyulu, J. Rao, Synth. Commun. 2000, 30, 2061.
-
(2000)
Synth. Commun.
, vol.30
, pp. 2061
-
-
Basavaiah, D.1
Krishnamacharyulu, M.2
Rao, J.3
-
42
-
-
4544352284
-
-
note
-
2. The details of these experiments will be reported in a separate full account.
-
-
-
-
43
-
-
4544253143
-
-
note
-
Several ligand-Lewis acid combinations were also evaluated. Of these, magnesium salts with ligand 9a gave the best results.
-
-
-
-
44
-
-
4544229295
-
-
note
-
3SiH; TMS = trimethylsilyl), tributyltin hydride gave the addition products most efficiently (clean with very few byproducts) and with the highest enantioselectivity.
-
-
-
-
45
-
-
4544246649
-
-
note
-
The catalytic loading was varied from 10 to 100 mol %. The enantioselectivity remained nearly constant (ca. 80% ee) for loadings between 20 and 75 mol %.
-
-
-
-
46
-
-
4544227235
-
-
note
-
The higher enantioselectivities observed for 8a and 8f at 30 mol % catalytic loading are not an experimental artifact. Further experimentation is required to identify the origin(s) of this anomaly.
-
-
-
-
47
-
-
0035929985
-
-
P. E. Coffey, K. Drauz, S. M. Roberts, J. Skidmore, J. A. Smith, Chem. Commun. 2001, 2330. See also ref. [3e]. Product 7a also has the S configuration (see the Supporting Information). By analogy, we assume that the face selectivity is the same for the other substrates.
-
(2001)
Chem. Commun.
, pp. 2330
-
-
Coffey, P.E.1
Drauz, K.2
Roberts, S.M.3
Skidmore, J.4
Smith, J.A.5
-
48
-
-
4544324375
-
-
note
-
This model is similar to that proposed by Metzger and coworkers in their work on diastereoselective H-atom transfer reactions with methylene glutarates (see ref. [7a]).
-
-
-
-
49
-
-
4544339027
-
-
note
-
At the present time we do not have a clear picture of the influence of the chiral ligand on the rotamer geometry of the ester substituent and its impact on the observed enantioselectivity.
-
-
-
-
51
-
-
0027385185
-
-
The size of the exocyclic substituent has been shown to have an impact on H-atom transfer reactions: B. Giese, W. Damm, T. Witzel, H.-G. Zeitz, Tetrahedron Lett. 1993, 34, 7053.
-
(1993)
Tetrahedron Lett.
, vol.34
, pp. 7053
-
-
Giese, B.1
Damm, W.2
Witzel, T.3
Zeitz, H.-G.4
|