-
1
-
-
0035977605
-
-
Bretscher, L. E.; Jenkins, C. L.; Taylor, K. M.; DeRider, M. L.; Raines, R. T. J. Am. Chem. Soc. 2001, 123, 777.
-
(2001)
J. Am. Chem. Soc.
, vol.123
, pp. 777
-
-
Bretscher, L.E.1
Jenkins, C.L.2
Taylor, K.M.3
DeRider, M.L.4
Raines, R.T.5
-
2
-
-
0032694325
-
-
(a) Prenner, E. J.; Lewis, R. N.; McElhaney, R. N. Biochim. Biophys. Acta 1999, 1462, 201-221.
-
(1999)
Biochim. Biophys. Acta
, vol.1462
, pp. 201-221
-
-
Prenner, E.J.1
Lewis, R.N.2
McElhaney, R.N.3
-
3
-
-
0021929603
-
-
(b) Tamaki, M.; Okitsu, T.; Araki, M.; Sakamoto, H.; Takimoto, M.; Muramatsu, I. Bull. Chem. Soc. Jpn. 1985, 58, 531.
-
(1985)
Bull. Chem. Soc. Jpn.
, vol.58
, pp. 531
-
-
Tamaki, M.1
Okitsu, T.2
Araki, M.3
Sakamoto, H.4
Takimoto, M.5
Muramatsu, I.6
-
4
-
-
0021285596
-
-
(a) Cody, W. L.; Wilkes, B. C.; Muska, B. J.; Hruby, V. J.; Castrucci, A. M.; Hadley, M. E. J. Med. Chem. 1984, 27, 1186.
-
(1984)
J. Med. Chem.
, vol.27
, pp. 1186
-
-
Cody, W.L.1
Wilkes, B.C.2
Muska, B.J.3
Hruby, V.J.4
Castrucci, A.M.5
Hadley, M.E.6
-
5
-
-
0002293913
-
-
(b) Hruby, V. J.; Wilkes, B. C.; Cody, W. L.; Sawyer, T. K.; Hadley, M. E. Pept. Protein Rev. 1984, 3, 1.
-
(1984)
Pept. Protein Rev.
, vol.3
, pp. 1
-
-
Hruby, V.J.1
Wilkes, B.C.2
Cody, W.L.3
Sawyer, T.K.4
Hadley, M.E.5
-
6
-
-
0037123418
-
-
Moriguchi, T.; Asai, N.; Okada, K.; Seio, K.; Sasaki, T.; Sekine, M. J. Org. Chem. 2002, 67, 3290.
-
(2002)
J. Org. Chem.
, vol.67
, pp. 3290
-
-
Moriguchi, T.1
Asai, N.2
Okada, K.3
Seio, K.4
Sasaki, T.5
Sekine, M.6
-
8
-
-
0019274399
-
-
Patchett, A. A.; Harris, E.; Tristram, E. W.; Wyvratt, M. J.; Wu, M. T.; Taub, D.; Peterson, E. R.; Ikeler, T. J.; Ten Broeke, J.; Payne, L. G. Ondeyka, D. L.; Thorsett, E. D.; Greenlee, W. J.; Lohr, N. S.; Hoffsommer, R. D.; Joshua, H.; Ruyle, W. V.; Rothrock, J. W.; Aster, S. D.; Maycock, A. L.; Robinson, F. M.; Hirschmann, R.; Sweet, C. S.; Ulm, E. H.; Gross, D. M.; Vassil, T. C.; Stone, C. A. Nature 1980, 288, 280.
-
(1980)
Nature
, vol.288
, pp. 280
-
-
Patchett, A.A.1
Harris, E.2
Tristram, E.W.3
Wyvratt, M.J.4
Wu, M.T.5
Taub, D.6
Peterson, E.R.7
Ikeler, T.J.8
Ten Broeke, J.9
Payne, L.G.10
Ondeyka, D.L.11
Thorsett, E.D.12
Greenlee, W.J.13
Lohr, N.S.14
Hoffsommer, R.D.15
Joshua, H.16
Ruyle, W.V.17
Rothrock, J.W.18
Aster, S.D.19
Maycock, A.L.20
Robinson, F.M.21
Hirschmann, R.22
Sweet, C.S.23
Ulm, E.H.24
Gross, D.M.25
Vassil, T.C.26
Stone, C.A.27
more..
-
9
-
-
0035906449
-
-
(a) Tamaki, M.; Han, G.; Hruby, V. J. J. Org. Chem. 2001, 66, 3593.
-
(2001)
J. Org. Chem.
, vol.66
, pp. 3593
-
-
Tamaki, M.1
Han, G.2
Hruby, V.J.3
-
10
-
-
0005761614
-
-
(b) Esslinger, C. S.; Koch, H. P.; Kavanaugh, M. P.; Philips, D. P.; Chamberlin, A. R.; Thompson, C. M.; Bridges, R. J. Bioorg. Med. Lett. 1998, 8, 3101.
-
(1998)
J. Bioorg. Med. Lett.
, vol.8
, pp. 3101
-
-
Esslinger, C.S.1
Koch, H.P.2
Kavanaugh, M.P.3
Philips, D.P.4
Chamberlin, A.R.5
Thompson, C.M.6
Bridges, R.7
-
11
-
-
0033576444
-
-
Han, W.; Pelletier, J. C.; Mersinger, L.; Ketner, C. A.; Hodge, C. N. Org. Lett. 1999, 1, 1875.
-
(1999)
Org. Lett.
, vol.1
, pp. 1875
-
-
Han, W.1
Pelletier, J.C.2
Mersinger, L.3
Ketner, C.A.4
Hodge, C.N.5
-
12
-
-
0029143240
-
-
Elliot, R. L.; Kopecka, H.; Lin, N.-H.; He, Y.; Garvey, D. S. Synthesis 1995, 772.
-
(1995)
Synthesis
, pp. 772
-
-
Elliot, R.L.1
Kopecka, H.2
Lin, N.-H.3
He, Y.4
Garvey, D.S.5
-
13
-
-
0442268049
-
-
Patent Application WO 98-KR246 19989898
-
Park, T. H.; Ha, Y. H.; Jeong, D. Y. Patent Application WO 98-KR246 19989898; Chem. Abstr. 1999, 130, 182388.
-
-
-
Park, T.H.1
Ha, Y.H.2
Jeong, D.Y.3
-
14
-
-
0005699488
-
-
Park, T. H.; Ha, Y. H.; Jeong, D. Y. Patent Application WO 98-KR246 19989898; Chem. Abstr. 1999, 130, 182388.
-
(1999)
Chem. Abstr.
, vol.130
, pp. 182388
-
-
-
15
-
-
33847086169
-
-
(a) Bell, E. A.; Qureshi, M. Y.; Pryce, R. J.; Janzen, D. H.; Lemke, P.; Clardy, J. J. Am. Chem. Soc. 1980, 109, 1409.
-
(1980)
J. Am. Chem. Soc.
, vol.109
, pp. 1409
-
-
Bell, E.A.1
Qureshi, M.Y.2
Pryce, R.J.3
Janzen, D.H.4
Lemke, P.5
Clardy, J.6
-
16
-
-
0001684338
-
-
(b) Talluri, S.; Montelione, B. T.; van Duyne, G.; Piela, L.; Clardy, J.; Scheraga, H. A. J. Am. Chem. Soc. 1987, 109, 4473.
-
(1987)
J. Am. Chem. Soc.
, vol.109
, pp. 4473
-
-
Talluri, S.1
Montelione, B.T.2
Van Duyne, G.3
Piela, L.4
Clardy, J.5
Scheraga, H.A.6
-
17
-
-
0001697266
-
-
(c) Piela, L.; Nemethy, G.; Scheraga, H. A. J. Am. Chem. Soc. 1987, 109, 4477.
-
(1987)
J. Am. Chem. Soc.
, vol.109
, pp. 4477
-
-
Piela, L.1
Nemethy, G.2
Scheraga, H.A.3
-
18
-
-
0000260041
-
-
(d) Montelione, G. T.; Hughes, P.; Clardy, J.; Scheraga, H. A. J. Am. Chem. Soc. 1986, 108, 6765.
-
(1986)
J. Am. Chem. Soc.
, vol.108
, pp. 6765
-
-
Montelione, G.T.1
Hughes, P.2
Clardy, J.3
Scheraga, H.A.4
-
19
-
-
0032514994
-
-
Krow, G. R.; Lee, Y. B.; Lester, W. S.; Christian, H.; Shaw, D. A.; Yuan, J. J. Org. Chem. 1998, 63, 8558.
-
(1998)
J. Org. Chem.
, vol.63
, pp. 8558
-
-
Krow, G.R.1
Lee, Y.B.2
Lester, W.S.3
Christian, H.4
Shaw, D.A.5
Yuan, J.6
-
22
-
-
0000679903
-
-
(c) Beak, P.; Basu, A.; Gallagher, D. J.; Park, Y. S.; Thayumanavan, S. Acc. Chem. Res. 1996, 29, 552.
-
(1996)
Acc. Chem. Res.
, vol.29
, pp. 552
-
-
Beak, P.1
Basu, A.2
Gallagher, D.J.3
Park, Y.S.4
Thayumanavan, S.5
-
25
-
-
0029822037
-
-
Regioselective α-lithiation of a tert-butylformamide at a dibenzylic bridgehead position in preference to a monobenzylic position has been reported. For other examples of related regioselective lithiation-substitution reactions, see: (b) Kopach, M. E.; Meyers, A. I. J. Org. Chem. 1996, 61, 6764.
-
(1996)
J. Org. Chem.
, vol.61
, pp. 6764
-
-
Kopach, M.E.1
Meyers, A.I.2
-
27
-
-
0001167606
-
-
(d) Coldham, I.; Copley, R. C. B.; Haxell, T. F. N.; Howard, S. Org. Lett. 2001, 3, 3799.
-
(2001)
Org. Lett.
, vol.3
, pp. 3799
-
-
Coldham, I.1
Copley, R.C.B.2
Haxell, T.F.N.3
Howard, S.4
-
28
-
-
0032211371
-
-
(e) Coldham, I.; Judkins, R. A.; Witty, D. R. Tetrahedron 1998, 54, 14255.
-
(1998)
Tetrahedron
, vol.54
, pp. 14255
-
-
Coldham, I.1
Judkins, R.A.2
Witty, D.R.3
-
31
-
-
0037178349
-
-
For calculated energies and favored geometries of α-lithioamides, see: (b) Wiberg, K. B.; Bailey, W. F. J. Org. Chem. 2002, 67, 5365.
-
(2002)
J. Org. Chem.
, vol.67
, pp. 5365
-
-
Wiberg, K.B.1
Bailey, W.F.2
-
32
-
-
0037028995
-
-
(c) Bailey, W. F.; Beak, P.; Kerrick, S. T.; Ma, S.; Wiberg, K. B. J. Am. Chem. Soc. 2002, 124, 1889.
-
(2002)
J. Am. Chem. Soc.
, vol.124
, pp. 1889
-
-
Bailey, W.F.1
Beak, P.2
Kerrick, S.T.3
Ma, S.4
Wiberg, K.B.5
-
36
-
-
0000720118
-
-
(g) Bach, R. D.; Braden, M. L.; Wolber, G. J. J. Org. Chem. 1983, 48, 1509.
-
(1983)
J. Org. Chem.
, vol.48
, pp. 1509
-
-
Bach, R.D.1
Braden, M.L.2
Wolber, G.J.3
-
37
-
-
0000058116
-
-
(h) Rondan, N. G.; Houk, K. N.; Beak, P.; Zajdel, W. J.; Chandrasekhar, J.; Schleyer, P. v. R. J. Org. Chem. 1981, 46, 4108.
-
(1981)
J. Org. Chem.
, vol.46
, pp. 4108
-
-
Rondan, N.G.1
Houk, K.N.2
Beak, P.3
Zajdel, W.J.4
Chandrasekhar, J.5
Schleyer, P.V.R.6
-
38
-
-
0013374665
-
-
For an alternative route to 3-substituted 2-azabicyclo[2.1.1 ]hexanes, see: (a) Krow, G. R.; Yuan, J.; Lin, G.; Sonnet, P. E. Org. Lett. 2002, 4, 1259. (b) Krow, G. R.; Lester, W. S.; Liu, N.; Yuan, J.; Hiller, A.; Duo, J.; Herzon, S. B.; Nguyen, Y.; Cannon, K. J. Org. Chem. 2001, 66, 1811. (c) Krow, G. R.; Lee, Y. B.; Lester, W. S.; Liu, N.; Yuan, J.; Duo, J.; Herzon, S. B.; Nguyen, Y.; Zacharias, D. J. Org. Chem. 2001, 66, 1805.
-
(2002)
Org. Lett.
, vol.4
, pp. 1259
-
-
Krow, G.R.1
Yuan, J.2
Lin, G.3
Sonnet, P.E.4
-
39
-
-
0035831145
-
-
For an alternative route to 3-substituted 2-azabicyclo[2.1.1 ]hexanes, see: (a) Krow, G. R.; Yuan, J.; Lin, G.; Sonnet, P. E. Org. Lett. 2002, 4, 1259. (b) Krow, G. R.; Lester, W. S.; Liu, N.; Yuan, J.; Hiller, A.; Duo, J.; Herzon, S. B.; Nguyen, Y.; Cannon, K. J. Org. Chem. 2001, 66, 1811. (c) Krow, G. R.; Lee, Y. B.; Lester, W. S.; Liu, N.; Yuan, J.; Duo, J.; Herzon, S. B.; Nguyen, Y.; Zacharias, D. J. Org. Chem. 2001, 66, 1805.
-
(2001)
J. Org. Chem.
, vol.66
, pp. 1811
-
-
Krow, G.R.1
Lester, W.S.2
Liu, N.3
Yuan, J.4
Hiller, A.5
Duo, J.6
Herzon, S.B.7
Nguyen, Y.8
Cannon, K.9
-
40
-
-
0035831229
-
-
For an alternative route to 3-substituted 2-azabicyclo[2.1.1 ]hexanes, see: (a) Krow, G. R.; Yuan, J.; Lin, G.; Sonnet, P. E. Org. Lett. 2002, 4, 1259. (b) Krow, G. R.; Lester, W. S.; Liu, N.; Yuan, J.; Hiller, A.; Duo, J.; Herzon, S. B.; Nguyen, Y.; Cannon, K. J. Org. Chem. 2001, 66, 1811. (c) Krow, G. R.; Lee, Y. B.; Lester, W. S.; Liu, N.; Yuan, J.; Duo, J.; Herzon, S. B.; Nguyen, Y.; Zacharias, D. J. Org. Chem. 2001, 66, 1805.
-
(2001)
J. Org. Chem.
, vol.66
, pp. 1805
-
-
Krow, G.R.1
Lee, Y.B.2
Lester, W.S.3
Liu, N.4
Yuan, J.5
Duo, J.6
Herzon, S.B.7
Nguyen, Y.8
Zacharias, D.9
-
41
-
-
0001411949
-
-
Saito, S.; Nakajima, H.; Inaba, M.; Moriwake, T. Tetrahedron Lett. 1989, 30, 837.
-
(1989)
Tetrahedron Lett.
, vol.30
, pp. 837
-
-
Saito, S.1
Nakajima, H.2
Inaba, M.3
Moriwake, T.4
-
42
-
-
0442263435
-
Carbon Dioxide
-
Paquette, L. A., Ed.; Wiley & Sons: New York
-
Mander, L. N. Carbon Dioxide. In Encyclopedia of Reagents for Organic Synthesis: Paquette, L. A., Ed.; Wiley & Sons: New York, 1995; pp 985-988.
-
(1995)
Encyclopedia of Reagents for Organic Synthesis
, pp. 985-988
-
-
Mander, L.N.1
-
43
-
-
85004388152
-
-
(a) Hashimoto, N.; Aoyama, T.; Shioiri, T. Chem. Pharm. Bull. 1981, 5, 1475.
-
(1981)
Chem. Pharm. Bull.
, vol.5
, pp. 1475
-
-
Hashimoto, N.1
Aoyama, T.2
Shioiri, T.3
-
44
-
-
33845282179
-
-
(b) Anelli, P. L.; Biffi, C.; Montanari, F.; Quici, S. J. Org. Chem. 1987, 52, 2559.
-
(1987)
J. Org. Chem.
, vol.52
, pp. 2559
-
-
Anelli, P.L.1
Biffi, C.2
Montanari, F.3
Quici, S.4
-
45
-
-
0442263431
-
-
note
-
2 afforded only bridgehead acid 8a (49%). Traces of water may have selectively quenched the 3-anion 5.
-
-
-
-
48
-
-
0001611404
-
-
(c) Hughes, P.; Martin, M.; Clardy, J. Tetrahedron Lett. 1980, 21, 4579.
-
(1980)
Tetrahedron Lett.
, vol.21
, pp. 4579
-
-
Hughes, P.1
Martin, M.2
Clardy, J.3
-
49
-
-
0442263434
-
-
note
-
2, gave erratic results. In one trial at -78 °C with sec-BuLi (1.6 equiv), azabicycle 4 afforded only aldehyde 8c (31%). In another trial, a 15:85 mixture of aldehydes 6c/8c (57%) was observed. Under the same conditions except with less base (1.05-1.10 equiv), there were numerous failures to observe any reaction; one trial gave unreacted 4/6c/8c = 67:0:33 (23%). These results may reflect selective quenching of the less stable 3-anion 5 with a proton source (water, dimethylamine?). In a trial in which reaction was allowed to continue overnight rather than 2 h, the 3-isomer was found to predominate: 6c/8c = 97:3 (41%). This result is consistent with the preferential loss of bridgehead aldehyde 8c noted during purification.
-
-
-
-
50
-
-
0442264987
-
-
note
-
3 exchange was observed in either case.
-
-
-
-
51
-
-
0000920450
-
-
Restricted rotation about the C-N bond of N-BOC pyrrolidine was presumed at -78 °C
-
(a) Beak, P.; Kerrick, S. T.; Wu, S.; Chu, J. J. Am. Chem. Soc. 1994, 116, 3231. Restricted rotation about the C-N bond of N-BOC pyrrolidine was presumed at -78 °C.
-
(1994)
J. Am. Chem. Soc.
, vol.116
, pp. 3231
-
-
Beak, P.1
Kerrick, S.T.2
Wu, S.3
Chu, J.4
-
52
-
-
0009709215
-
-
An N-COOMe rotational barrier of 16 kcal/mol was determined at -3 °C
-
(b) Price, B. J.; Smallman, R. V.; Sutherland, I. O. Chem. Commun. 1966, 319. An N-COOMe rotational barrier of 16 kcal/mol was determined at -3 °C.
-
(1966)
Chem. Commun.
, pp. 319
-
-
Price, B.J.1
Smallman, R.V.2
Sutherland, I.O.3
-
53
-
-
0028238053
-
-
See ref 27 therein in comparing carbamates to amides: "few amides have rotational barriers of less than 15 kcal/mol and coordination of the carbonyl raises the barrier."
-
(c) Gawley, R. E.; Zhang, Q. Tetrahedron 1994, 50, 6077. See ref 27 therein in comparing carbamates to amides: "few amides have rotational barriers of less than 15 kcal/mol and coordination of the carbonyl raises the barrier."
-
(1994)
Tetrahedron
, vol.50
, pp. 6077
-
-
Gawley, R.E.1
Zhang, Q.2
-
54
-
-
0004133516
-
-
Gaussian, Inc.; Pittsburgh, PA
-
Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Zakrzewski, V. G.; Montgomery, J. A., Jr.; Stratmann, R. E.; Burant, J. C.; Dapprich, S.; Millam, J. M.; Daniels, A. D.; Kudin, K. N.; Strain, M. C.; Farkas, O.; Tomasi, J.; Barone, V.; Cossi, M.; Cammi, R.; Mennucci, B.; Pomelli, C.; Adamo, C.; Clifford, S.; Ochterski, J.; Petersson, G. A.; Ayala, P. Y.; Cui, Q.; Morokuma, K.; Malick, D. K.; Rabuck, A. D.; Raghavachari, K.; Foresman, J. B.; Cioslowski, J.; Ortiz, J. V.; Stefanov, B. B.; Liu, G.; Liashenko, A.; Piskorz, P.; Komaromi, I.; Gomperts, R.; Martin, R. L.; Fox, D. J.; Keith, T.; Al-Laham, M. A.; Peng, C. Y.; Nanayakkara, A.; Gonzalez, C.; Challacombe, M.; Gill, P. M. W.; Johnson, B. G.; Chen, W.; Wong, M. W.; Andres, J. L.; Head-Gordon, M.; Replogle, E. S.; Pople, J. A. Gaussian 98, revision A.9; Gaussian, Inc.; Pittsburgh, PA, 1998.
-
(1998)
Gaussian 98, Revision A.9
-
-
Frisch, M.J.1
Trucks, G.W.2
Schlegel, H.B.3
Scuseria, G.E.4
Robb, M.A.5
Cheeseman, J.R.6
Zakrzewski, V.G.7
Montgomery Jr., J.A.8
Stratmann, R.E.9
Burant, J.C.10
Dapprich, S.11
Millam, J.M.12
Daniels, A.D.13
Kudin, K.N.14
Strain, M.C.15
Farkas, O.16
Tomasi, J.17
Barone, V.18
Cossi, M.19
Cammi, R.20
Mennucci, B.21
Pomelli, C.22
Adamo, C.23
Clifford, S.24
Ochterski, J.25
Petersson, G.A.26
Ayala, P.Y.27
Cui, Q.28
Morokuma, K.29
Malick, D.K.30
Rabuck, A.D.31
Raghavachari, K.32
Foresman, J.B.33
Cioslowski, J.34
Ortiz, J.V.35
Stefanov, B.B.36
Liu, G.37
Liashenko, A.38
Piskorz, P.39
Komaromi, I.40
Gomperts, R.41
Martin, R.L.42
Fox, D.J.43
Keith, T.44
Al-Laham, M.A.45
Peng, C.Y.46
Nanayakkara, A.47
Gonzalez, C.48
Challacombe, M.49
Gill, P.M.W.50
Johnson, B.G.51
Chen, W.52
Wong, M.W.53
Andres, J.L.54
Head-Gordon, M.55
Replogle, E.S.56
Pople, J.A.57
more..
-
55
-
-
0442263433
-
-
note
-
16c are somewhat pyramidal.
-
-
-
-
57
-
-
0033623224
-
-
Beak, P.; Anderson, D. R.; Curtis, M. D.; Laumer, J. M.; Pippel, D. J.; Weisenburger, G. A. Acc. Chem. Res. 2000, 33, 715.
-
(2000)
Acc. Chem. Res.
, vol.33
, pp. 715
-
-
Beak, P.1
Anderson, D.R.2
Curtis, M.D.3
Laumer, J.M.4
Pippel, D.J.5
Weisenburger, G.A.6
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