-
1
-
-
33947468159
-
-
(a) Winstein, S.; Clippinger, E.; Fainberg, A. H.; Heck, R.; Robinson, G. C. J. Am. Chem. Soc. 1956, 78, 328.
-
(1956)
J. Am. Chem. Soc.
, vol.78
, pp. 328
-
-
Winstein, S.1
Clippinger, E.2
Fainberg, A.H.3
Heck, R.4
Robinson, G.C.5
-
2
-
-
0000856920
-
-
Szwarc, M., Ed.; Wiley: New York
-
(b) Raber, D. J.; Harris, J. M.; Schleyer, P. v. R. In Ions and Ion Pairs in Organic Reactions; Szwarc, M., Ed.; Wiley: New York, 1974; Vol. 2, p 247.
-
(1974)
Ions and Ion Pairs in Organic Reactions
, vol.2
, pp. 247
-
-
Raber, D.J.1
Harris, J.M.2
Schleyer, P.V.R.3
-
3
-
-
33947708736
-
-
(c) Richard, J. P.; Amyes, T. L.; Toteva, M. M.; Tsuji, Y. Adv. Phys. Org. Chem. 2004, 39, 1.
-
(2004)
Adv. Phys. Org. Chem.
, vol.39
, pp. 1
-
-
Richard, J.P.1
Amyes, T.L.2
Toteva, M.M.3
Tsuji, Y.4
-
4
-
-
7244245511
-
-
For a recent example from our own laboratory, see: Crich, D.; Chandrasekera, N. S. Angew. Chem., Int. Ed. 2004, 43, 5386.
-
(2004)
Angew. Chem., Int. Ed.
, vol.43
, pp. 5386
-
-
Crich, D.1
Chandrasekera, N.S.2
-
5
-
-
0032503553
-
-
For recent examples, see: (a) Buckmelter, A. J.; Powers, J. P.; Rychnovsky, S. D. J. Am. Chem. Soc. 1998, 120, 5589.
-
(1998)
J. Am. Chem. Soc.
, vol.120
, pp. 5589
-
-
Buckmelter, A.J.1
Powers, J.P.2
Rychnovsky, S.D.3
-
6
-
-
0034605472
-
-
(b) Buckmelter, A. J.; Kim, A. I.; Rychnovsky, S. D. J. Am. Chem. Soc. 2000, 122, 9386.
-
(2000)
J. Am. Chem. Soc.
, vol.122
, pp. 9386
-
-
Buckmelter, A.J.1
Kim, A.I.2
Rychnovsky, S.D.3
-
8
-
-
0003320995
-
-
(d) Rychnovsky, S. D.; Hata, T.; Kim, A. I.; Buckmelter, A. J. Org. Lett. 2001, 3, 807.
-
(2001)
Org. Lett.
, vol.3
, pp. 807
-
-
Rychnovsky, S.D.1
Hata, T.2
Kim, A.I.3
Buckmelter, A.J.4
-
9
-
-
22144458811
-
-
(e) Sauer, S.; Schumacher, A.; Barbosa, F. G. B. Tetrahedron Lett. 1998, 39, 685.
-
(1998)
Tetrahedron Lett.
, vol.39
, pp. 685
-
-
Sauer, S.1
Schumacher, A.2
Barbosa, F.G.B.3
-
10
-
-
0033520303
-
-
(f) Giese, B.; Wettstein, P.; Stahelin, C.; Barbosa, F.; Neuberger, M.; Zehnder, M.; Wessig, P. Angew. Chem., Int. Ed. 1999, 38, 2586.
-
(1999)
Angew. Chem., Int. Ed.
, vol.38
, pp. 2586
-
-
Giese, B.1
Wettstein, P.2
Stahelin, C.3
Barbosa, F.4
Neuberger, M.5
Zehnder, M.6
Wessig, P.7
-
12
-
-
0031573815
-
-
For reviews, see: (a) Schmittel, M.; Burghart, A. Angew. Chem., Int. Ed. Engl. 1997, 36, 2550.
-
(1997)
Angew. Chem., Int. Ed. Engl.
, vol.36
, pp. 2550
-
-
Schmittel, M.1
Burghart, A.2
-
13
-
-
0002025512
-
-
Mattay, J., Ed.; Springer: Berlin
-
(b) Hintz, S.; Heidbreder, A.; Mattay, J. In Topics in Current Chemistry: Mattay, J., Ed.; Springer: Berlin, 1996; Vol. 177, p 77.
-
(1996)
Topics in Current Chemistry
, vol.177
, pp. 77
-
-
Hintz, S.1
Heidbreder, A.2
Mattay, J.3
-
14
-
-
0344901362
-
-
(c) Bauld, N. L.; Bellville, D. J.; Harirchian, B.; Lorenz, K. T.; Pabon, R. A.; Reynolds, D. W.; Wirth, D, D.; Chiou, H.-S.; Marsh, B. K. Acc. Chem. Res. 1987, 20, 371.
-
(1987)
Acc. Chem. Res.
, vol.20
, pp. 371
-
-
Bauld, N.L.1
Bellville, D.J.2
Harirchian, B.3
Lorenz, K.T.4
Pabon, R.A.5
Reynolds, D.W.6
Wirth, D.D.7
Chiou, H.-S.8
Marsh, B.K.9
-
15
-
-
0000697108
-
-
(a) Beckwith, A. L. J.; Crich, D.; Duggan, P. J.; Yao, Q. Chem. Rev. 1997, 97, 3273.
-
(1997)
Chem. Rev.
, vol.97
, pp. 3273
-
-
Beckwith, A.L.J.1
Crich, D.2
Duggan, P.J.3
Yao, Q.4
-
16
-
-
0001271574
-
-
Renaud, P., Sibi, M., Eds.; Wiley-VCH: Weinheim
-
(b) Crich, D. In Radicals in Organic Synthesis; Renaud, P., Sibi, M., Eds.; Wiley-VCH: Weinheim, 2001; Vol. 2, p 188.
-
(2001)
Radicals in Organic Synthesis
, vol.2
, pp. 188
-
-
Crich, D.1
-
17
-
-
0033601068
-
-
(a) Newcomb, M.; Horner, J. H.; Whitted, P. O.; Crich, D.; Huang, X.; Yao, Q.; Zipse, H. J. Am. Chem. Soc. 1999, 121, 10685.
-
(1999)
J. Am. Chem. Soc.
, vol.121
, pp. 10685
-
-
Newcomb, M.1
Horner, J.H.2
Whitted, P.O.3
Crich, D.4
Huang, X.5
Yao, Q.6
Zipse, H.7
-
18
-
-
0033564989
-
-
(b) Whitted, P. O.; Horner, J. H.; Newcomb, M.; Huang, X.; Crich, D. Org. Lett. 1999, 1, 153.
-
(1999)
Org. Lett.
, vol.1
, pp. 153
-
-
Whitted, P.O.1
Horner, J.H.2
Newcomb, M.3
Huang, X.4
Crich, D.5
-
19
-
-
0034835791
-
-
(c) Bales, B. C.; Horner, J. H.; Huang, X.; Newcomb, M.; Crich, D.; Greenberg, M. M. J. Am. Chem. Soc. 2001, 123, 3623.
-
(2001)
J. Am. Chem. Soc.
, vol.123
, pp. 3623
-
-
Bales, B.C.1
Horner, J.H.2
Huang, X.3
Newcomb, M.4
Crich, D.5
Greenberg, M.M.6
-
20
-
-
0034725380
-
-
(d) Newcomb, M.; Miranda, N.; Huang, X.; Crich, D. J. Am. Chem. Soc. 2000, 122, 6128.
-
(2000)
J. Am. Chem. Soc.
, vol.122
, pp. 6128
-
-
Newcomb, M.1
Miranda, N.2
Huang, X.3
Crich, D.4
-
21
-
-
0347916936
-
-
(e) Bagnol, L.; Horner, J. H.; Newcomb, M. Org. Lett. 2003, 5, 5055.
-
(2003)
Org. Lett.
, vol.5
, pp. 5055
-
-
Bagnol, L.1
Horner, J.H.2
Newcomb, M.3
-
22
-
-
8844287513
-
-
(f) Horner, J. H.; Bagnol, L.; Newcomb, M. J. Am. Chem. Soc. 2004, 126, 14979.
-
(2004)
J. Am. Chem. Soc.
, vol.126
, pp. 14979
-
-
Horner, J.H.1
Bagnol, L.2
Newcomb, M.3
-
23
-
-
1842737688
-
-
(g) Wang, Y.; Grimme, S.; Zipse, H. J. Phys. Chem. A 2004, 108, 2324.
-
(2004)
J. Phys. Chem. A
, vol.108
, pp. 2324
-
-
Wang, Y.1
Grimme, S.2
Zipse, H.3
-
27
-
-
0001264344
-
-
(c) Crich, D.; Yao, Q.; Filzen, G. F. J. Am. Chem. Soc. 1995, 117, 11455.
-
(1995)
J. Am. Chem. Soc.
, vol.117
, pp. 11455
-
-
Crich, D.1
Yao, Q.2
Filzen, G.F.3
-
28
-
-
0037123672
-
-
(d) Crich, D.; Sartillo-Piscil, F.; Quintero-Cortes, L.; Wink, D. J. J. Org. Chem. 2002, 67, 3360.
-
(2002)
J. Org. Chem.
, vol.67
, pp. 3360
-
-
Crich, D.1
Sartillo-Piscil, F.2
Quintero-Cortes, L.3
Wink, D.J.4
-
32
-
-
33747565073
-
-
(c) Giese, B.; Beyrich-Graf, X.; Burger, J.; Kesselheim, C.; Senn, M.; Schafer, T. Angew. Chem., Int. Ed. Engl. 1993, 32, 1742.
-
(1993)
Angew. Chem., Int. Ed. Engl.
, vol.32
, pp. 1742
-
-
Giese, B.1
Beyrich-Graf, X.2
Burger, J.3
Kesselheim, C.4
Senn, M.5
Schafer, T.6
-
33
-
-
0034723342
-
-
(d) Crich, D.; Huang, X.; Newcomb, M. J. Org. Chem. 2000, 65, 523.
-
(2000)
J. Org. Chem.
, vol.65
, pp. 523
-
-
Crich, D.1
Huang, X.2
Newcomb, M.3
-
36
-
-
0642337274
-
-
Arnold, B. R.; Noukakis, D.; Farid, S.; Goodman, J. L.; Gould, I. R. J. Am. Chem. Soc. 1995, 117, 4399.
-
(1995)
J. Am. Chem. Soc.
, vol.117
, pp. 4399
-
-
Arnold, B.R.1
Noukakis, D.2
Farid, S.3
Goodman, J.L.4
Gould, I.R.5
-
37
-
-
22144489616
-
-
note
-
In this paper, nitrophosphates and their precursors are numbered as indicated. The N-benzyl group is considered part of the extended zigzag conformation backbone, and all methyl groups are considered substituents. For purposes of consistency throughout the paper, this system is applied even to compounds 3, 5, and 6, which would be more correctly shown with the methyl group as part of the backbone and the amine as a substituent. (diagram presented)
-
-
-
-
38
-
-
22144466670
-
-
note
-
No significant difference was observed on the product ratios, whether determined on the crude reaction mixtures or following the extractive workup.
-
-
-
-
39
-
-
0038540780
-
-
Crich, D.; Ranganathan, K.; Neelamkavil, S.; Huang, X. J. Am. Chem. Soc. 2003, 125, 7942.
-
(2003)
J. Am. Chem. Soc.
, vol.125
, pp. 7942
-
-
Crich, D.1
Ranganathan, K.2
Neelamkavil, S.3
Huang, X.4
-
40
-
-
22144459531
-
-
note
-
14
-
-
-
-
41
-
-
22144487829
-
-
note
-
In the trisubstituted pyrrolidines 11-13, the first stereochemical descriptor refers to the relationship between the isopropyl group on the 2-position and the next substituent around the ring. The second stereochemical descriptor applies to the relationship between the two methyl groups; thus, for example, cis,trans-11 refers to 2,3-cis-3,4-trans-1-benzyl-2-isopropyl-3,4- dimethylpyrrolidine.
-
-
-
-
42
-
-
22144437849
-
-
note
-
It should be noted, however, that 1,3-diaxial interactions are less important in chair-like transition states with their longer partial bonds than in actual chair form rings, which leaves open the possibility that these cyclizations may occur through the chair-like transition states.
-
-
-
-
43
-
-
22144478019
-
-
note
-
In this scheme, anti,anti-6 and trans,cis-13, and the associated transition states, are represented as their enantiomers for ease of comparison.
-
-
-
-
49
-
-
0000782249
-
-
Renaud, P., Sibi, M. P., Eds.; Wiley-VCH: Weinheim
-
(b) Newcomb, M. In Radicals in Organic Synthesis; Renaud, P., Sibi, M. P., Eds.; Wiley-VCH: Weinheim, 2001; Vol. 1, p 317.
-
(2001)
Radicals in Organic Synthesis
, vol.1
, pp. 317
-
-
Newcomb, M.1
-
51
-
-
2442630750
-
-
Current thinking suggests that the cyclohexadienyl radical resulting from the second cyclization is oxidized by the initiator AIBN: (a) Beckwith, A. L. J.; Bowry, V. W.; Bowman, W. R.; Mann, E.; Parr, J.; Storey, J. M. D. Angew. Chem., Int. Ed. 2004, 43, 95.
-
(2004)
Angew. Chem., Int. Ed.
, vol.43
, pp. 95
-
-
Beckwith, A.L.J.1
Bowry, V.W.2
Bowman, W.R.3
Mann, E.4
Parr, J.5
Storey, J.M.D.6
-
53
-
-
0028235518
-
-
(c) Curran, D. P.; Yu, H.; Liu, H. Tetrahedron 1994, 50, 7343.
-
(1994)
Tetrahedron
, vol.50
, pp. 7343
-
-
Curran, D.P.1
Yu, H.2
Liu, H.3
-
55
-
-
22144459907
-
-
note
-
Presumably, these oxidative cyclizations take place at the level of the pyrrolidinium ion arising from the first cyclization, suggesting that the configuration at nitrogen and possibly even the bulk: of the associated phosphate anion must be taken into account in any model.
-
-
-
|