-
1
-
-
0020407132
-
-
For examples of bioactive 1,3-amino alcohols, see: (a) Wang, Y.-F, Izawa, T, Kobayashi, S, Ohno, M. J. Am. Chem. Soc. 1982, 104, 6465
-
For examples of bioactive 1,3-amino alcohols, see: (a) Wang, Y.-F.; Izawa, T.; Kobayashi, S.; Ohno, M. J. Am. Chem. Soc. 1982, 104, 6465.
-
-
-
-
2
-
-
33748225492
-
-
(b) Benz, G.; Henning, R.; Stasch, J.-P. Angew. Chem., Int. Ed. 1991, 30, 1702.
-
(1991)
Angew. Chem., Int. Ed
, vol.30
, pp. 1702
-
-
Benz, G.1
Henning, R.2
Stasch, J.-P.3
-
3
-
-
0026740226
-
-
(c) Boyd, S. A.; Fung, A. K. L.; Baker, W. R.; Mantei, R. A.; Armiger, Y.-L.; Stein, H. H.; Cohen, J.; Egan, D. A.; Barlow, J. L.; Klinghofer, V.; Verburg, K. M.; Martin, D. L.; Young, G. A.; Polakowski, J. S.; Hoffman, D. J.; Garren, K. W.; Perun, T. J.; Kleinert, H. D. J. Med. Chem. 1992, 35, 1735.
-
(1992)
J. Med. Chem
, vol.35
, pp. 1735
-
-
Boyd, S.A.1
Fung, A.K.L.2
Baker, W.R.3
Mantei, R.A.4
Armiger, Y.-L.5
Stein, H.H.6
Cohen, J.7
Egan, D.A.8
Barlow, J.L.9
Klinghofer, V.10
Verburg, K.M.11
Martin, D.L.12
Young, G.A.13
Polakowski, J.S.14
Hoffman, D.J.15
Garren, K.W.16
Perun, T.J.17
Kleinert, H.D.18
-
4
-
-
0029928601
-
-
(d) Jacobi, P. A.; Murphree, S.; Rupprecht, F.; Zheng, W. J. Org. Chem. 1996, 61, 2413.
-
(1996)
J. Org. Chem
, vol.61
, pp. 2413
-
-
Jacobi, P.A.1
Murphree, S.2
Rupprecht, F.3
Zheng, W.4
-
5
-
-
4344689901
-
-
(e) Steinmetz, H.; Glaser, N.; Herdtweck, E.; Sasse, F.; Reichenbach, H.; Höfle, G. Angew. Chem., Int. Ed. 2004, 43, 4888.
-
(2004)
Angew. Chem., Int. Ed
, vol.43
, pp. 4888
-
-
Steinmetz, H.1
Glaser, N.2
Herdtweck, E.3
Sasse, F.4
Reichenbach, H.5
Höfle, G.6
-
6
-
-
37049067428
-
-
For previous approaches to the chiral 1,3-amino alcohol functionality, which are however not as short and convergent as the one-described herein, see: a
-
For previous approaches to the chiral 1,3-amino alcohol functionality, which are however not as short and convergent as the one-described herein, see: (a) Pilli, R. A.; Russowsky, D.; Dias, L. C. Chem. Commun. 1987, 14, 1053.
-
(1987)
Chem. Commun
, vol.14
, pp. 1053
-
-
Pilli, R.A.1
Russowsky, D.2
Dias, L.C.3
-
7
-
-
37049077809
-
-
(b) Pilli, R. A.; Russowsky, D.; Dias, L. C. J. Chem. Soc., Perkin Trans. 1 1990, 1213.
-
(1990)
J. Chem. Soc., Perkin Trans. 1
, pp. 1213
-
-
Pilli, R.A.1
Russowsky, D.2
Dias, L.C.3
-
10
-
-
0037195685
-
-
(e) Benedetti, F.; Berti, F.; Norbedo, S. J. Org. Chem. 2002, 67, 8635.
-
(2002)
J. Org. Chem
, vol.67
, pp. 8635
-
-
Benedetti, F.1
Berti, F.2
Norbedo, S.3
-
11
-
-
30944461014
-
-
(f) Adamo, I.; Benedetti, F.; Berti, F.; Campaner, P. Org. Lett. 2006, 8, 51.
-
(2006)
Org. Lett
, vol.8
, pp. 51
-
-
Adamo, I.1
Benedetti, F.2
Berti, F.3
Campaner, P.4
-
12
-
-
0003495415
-
-
For reviews, see: a, Georg Thieme Verlag: Stuttgart
-
For reviews, see: (a) Martens, J. Methods of Organic Chemistry (Houben-Weyl); Georg Thieme Verlag: Stuttgart, 1995; Vol. E21d, p 4199.
-
(1995)
Methods of Organic Chemistry (Houben-Weyl)
, vol.E21d
, pp. 4199
-
-
Martens, J.1
-
14
-
-
0345044510
-
-
(c) Gomez, S.; Peters, J. A.; Maschmeyer, T. Adv. Synth. Catal. 2002, 344, 1037.
-
(2002)
Adv. Synth. Catal
, vol.344
, pp. 1037
-
-
Gomez, S.1
Peters, J.A.2
Maschmeyer, T.3
-
15
-
-
0000899213
-
-
More recent examples are described in: (a) Apodaca, R.; Xiao, W. Org. Lett. 2001, 3, 1745.
-
More recent examples are described in: (a) Apodaca, R.; Xiao, W. Org. Lett. 2001, 3, 1745.
-
-
-
-
16
-
-
0035908214
-
-
(b) Allegretti, M.; Berdini, V.; Candida Cesra, M.; Curti, R.; Nicolini, L.; Topai, A. Tetrahedron Lett. 2001, 42, 4257.
-
(2001)
Tetrahedron Lett
, vol.42
, pp. 4257
-
-
Allegretti, M.1
Berdini, V.2
Candida Cesra, M.3
Curti, R.4
Nicolini, L.5
Topai, A.6
-
17
-
-
0012975811
-
-
(c) Gross, T.; Seayad, A. M.; Ahmad, M.; Beller, M. Org. Lett. 2002, 4, 2055.
-
(2002)
Org. Lett
, vol.4
, pp. 2055
-
-
Gross, T.1
Seayad, A.M.2
Ahmad, M.3
Beller, M.4
-
18
-
-
0742324457
-
-
(d) Miriyala, B.; Bhattacharyya, S.; Williamson, J. S. Tetrahedron 2004, 60, 1463.
-
(2004)
Tetrahedron
, vol.60
, pp. 1463
-
-
Miriyala, B.1
Bhattacharyya, S.2
Williamson, J.S.3
-
19
-
-
4143066159
-
-
(e) Itoh, T.; Nagata, K.; Miyazaki, M.; Ishikawa, H.; Kurihara, A.; Ohsawa, A. Tetrahedron 2004, 60, 6649.
-
(2004)
Tetrahedron
, vol.60
, pp. 6649
-
-
Itoh, T.1
Nagata, K.2
Miyazaki, M.3
Ishikawa, H.4
Kurihara, A.5
Ohsawa, A.6
-
20
-
-
33644771025
-
-
(f) Menche, D.; Hassfeld, J.; Li, J.; Menche, G.; Ritter, A.; Rudolph, S. Org. Lett. 2006, 8, 741.
-
(2006)
Org. Lett
, vol.8
, pp. 741
-
-
Menche, D.1
Hassfeld, J.2
Li, J.3
Menche, G.4
Ritter, A.5
Rudolph, S.6
-
21
-
-
13844294033
-
-
For a review of direct asymmetric reductive animations, see
-
For a review of direct asymmetric reductive animations, see: Tararov, V. I.; Börner, A. Synlett 2005, 203.
-
(2005)
Synlett
, pp. 203
-
-
Tararov, V.I.1
Börner, A.2
-
22
-
-
0033017113
-
-
For auxiliary-mediated variants, see: a
-
For auxiliary-mediated variants, see: (a) Blaser, H.-U.; Buser, H.-P.; Jalett, H. P.; Pugin, B.; Spindler, F. Synlett 1999, 867.
-
(1999)
Synlett
, pp. 867
-
-
Blaser, H.-U.1
Buser, H.-P.2
Jalett, H.P.3
Pugin, B.4
Spindler, F.5
-
23
-
-
0345276532
-
-
(b) Kadyrov, R.; Riermeier, T. H. Angew. Chem., Int. Ed. 2003, 42, 5472.
-
(2003)
Angew. Chem., Int. Ed
, vol.42
, pp. 5472
-
-
Kadyrov, R.1
Riermeier, T.H.2
-
24
-
-
2542458280
-
-
(c) Tararov, V. I.; Kadyrov, R.; Riermeier, T. H.; Fischer, C.; Börner, A. Adv. Synth. Catal. 2004, 346, 561.
-
(2004)
Adv. Synth. Catal
, vol.346
, pp. 561
-
-
Tararov, V.I.1
Kadyrov, R.2
Riermeier, T.H.3
Fischer, C.4
Börner, A.5
-
25
-
-
0038626742
-
-
(d) Chi, Y. X.; Zhou, Y. G.; Zhang, X. M. J. Org. Chem. 2003, 68, 4120.
-
(2003)
J. Org. Chem
, vol.68
, pp. 4120
-
-
Chi, Y.X.1
Zhou, Y.G.2
Zhang, X.M.3
-
26
-
-
30744477746
-
-
(e) Storer, R. I.; Carrera, D. E.; Ni, Y.; MacMillan, D. W. C. J. Am. Chem. Soc. 2006, 128, 84.
-
(2006)
J. Am. Chem. Soc
, vol.128
, pp. 84
-
-
Storer, R.I.1
Carrera, D.E.2
Ni, Y.3
MacMillan, D.W.C.4
-
27
-
-
0000844109
-
-
Asymmetric animations of cyclic ketones have been reported: (a) Abdel-Magid, A. F.; Carson, K. G.; Harris, B. D.; Maryanoff, C. A.; Shah, R. D. J. Org. Chem. 1996, 61, 3849.
-
Asymmetric animations of cyclic ketones have been reported: (a) Abdel-Magid, A. F.; Carson, K. G.; Harris, B. D.; Maryanoff, C. A.; Shah, R. D. J. Org. Chem. 1996, 61, 3849.
-
-
-
-
28
-
-
0344944866
-
-
(b) Williams, G. D.; Pike, R. A.; Wade, C. E.; Wills, M. Org. Lett. 2003, 5, 4227.
-
(2003)
Org. Lett
, vol.5
, pp. 4227
-
-
Williams, G.D.1
Pike, R.A.2
Wade, C.E.3
Wills, M.4
-
31
-
-
33746679902
-
-
Asymmetric reductive aminations with chiral amines are reported by
-
Asymmetric reductive aminations with chiral amines are reported by: Nugent, T. C.; Ghosh, A. K.; Wakchaure, V. N.; Mohanty, R. R. Adv. Synth. Catal. 2006, 348, 1289.
-
(2006)
Adv. Synth. Catal
, vol.348
, pp. 1289
-
-
Nugent, T.C.1
Ghosh, A.K.2
Wakchaure, V.N.3
Mohanty, R.R.4
-
34
-
-
0008583584
-
-
Kempf, D. J.; Sham, H. L.; Marsh, K. C.; Flentge, C. A.; Betebenner, D.; Green, B. E.; McDonald, E.; Vasavanonda, S.; Saldivar, A.; Wideburg, N. E.; Kati, W. M.; Ruiz, L.; Zhao, C.; Fino, L.; Patterson, J.; Molla, A.; Plattner, J. J.; Norbeck, D. W. J. Med. Chem. 1998, 41, 602.
-
(1998)
J. Med. Chem
, vol.41
, pp. 602
-
-
Kempf, D.J.1
Sham, H.L.2
Marsh, K.C.3
Flentge, C.A.4
Betebenner, D.5
Green, B.E.6
McDonald, E.7
Vasavanonda, S.8
Saldivar, A.9
Wideburg, N.E.10
Kati, W.M.11
Ruiz, L.12
Zhao, C.13
Fino, L.14
Patterson, J.15
Molla, A.16
Plattner, J.J.17
Norbeck, D.W.18
-
35
-
-
0031788930
-
-
Sham, H. L.; Kempf, D. J.; Molla, A.; Marsh, K. C.; Kumar, G. N.; Chen, C. M.; Kati, W.; Stewart, K.; Lal, R.; Hsu, A.; Betebenner, D.; Korneyeva, M.; Vasavanonda, S.; McDonald, E.; Saldivar, A.; Wideburg, N.; Chen, X.; Niu, P.; Park, C.; Jayanti, V.; Grabowski, B.; Granneman, G. R.; Sun, E.; Japour, A. J.; Leonard, J. M.; Plattner, J. J.; Norbeck, D. W. Antimicrob. Agents Chemother. 1998, 42, 3218.
-
(1998)
Antimicrob. Agents Chemother
, vol.42
, pp. 3218
-
-
Sham, H.L.1
Kempf, D.J.2
Molla, A.3
Marsh, K.C.4
Kumar, G.N.5
Chen, C.M.6
Kati, W.7
Stewart, K.8
Lal, R.9
Hsu, A.10
Betebenner, D.11
Korneyeva, M.12
Vasavanonda, S.13
McDonald, E.14
Saldivar, A.15
Wideburg, N.16
Chen, X.17
Niu, P.18
Park, C.19
Jayanti, V.20
Grabowski, B.21
Granneman, G.R.22
Sun, E.23
Japour, A.J.24
Leonard, J.M.25
Plattner, J.J.26
Norbeck, D.W.27
more..
-
36
-
-
33846605606
-
-
For related conditions for direct reductive aminations of carbonyls, see: (a) entry 1, ref 4a
-
For related conditions for direct reductive aminations of carbonyls, see: (a) entry 1, ref 4a.
-
-
-
-
37
-
-
0031451535
-
Entry 2: Bhattacharyya, S
-
(b) Entry 2: Bhattacharyya, S. Synth. Commun. 1997, 27, 4265.
-
(1997)
Synth. Commun
, vol.27
, pp. 4265
-
-
-
38
-
-
33846596233
-
-
Entry 3: ref 4e
-
(c) Entry 3: ref 4e.
-
-
-
-
39
-
-
4043071644
-
-
Entry 4: Borch, R. F.; Bernstein, M. D.; Durst, H. D. J. Am. Chem. Soc. 1971, 93, 2897.
-
(d) Entry 4: Borch, R. F.; Bernstein, M. D.; Durst, H. D. J. Am. Chem. Soc. 1971, 93, 2897.
-
-
-
-
40
-
-
33846585068
-
-
Entry 5: ref 4f
-
(e) Entry 5: ref 4f.
-
-
-
-
41
-
-
0032724354
-
-
Entry 6: Bhattacharyya, S.; Neidigh, K. A.; Avery, M. A.; Williamson, J. S. Synlett 1999, 1781.
-
(f) Entry 6: Bhattacharyya, S.; Neidigh, K. A.; Avery, M. A.; Williamson, J. S. Synlett 1999, 1781.
-
-
-
-
42
-
-
33846619253
-
-
Stereochemical assignment of 9 and 10 was based on J-based configurational analysis and confirmed by NMR analysis of a cyclic derivative (see Supporting Information): (Chemical Equation Presented)
-
Stereochemical assignment of 9 and 10 was based on J-based configurational analysis and confirmed by NMR analysis of a cyclic derivative (see Supporting Information): (Chemical Equation Presented)
-
-
-
-
44
-
-
33846578775
-
-
For experimental details, spectral data, HPLC traces, and copies of NMR spectra for all new compounds, see Supporting Information
-
For experimental details, spectral data, HPLC traces, and copies of NMR spectra for all new compounds, see Supporting Information.
-
-
-
-
45
-
-
0001790298
-
-
For a review on asymmetric boron-mediated aldol reactions, see
-
For a review on asymmetric boron-mediated aldol reactions, see: Cowden, C. J.; Paterson, I. Org. React. 1997, 51, 1.
-
(1997)
Org. React
, vol.51
, pp. 1
-
-
Cowden, C.J.1
Paterson, I.2
|