-
1
-
-
2642675659
-
-
For reviews on the Prins cyclization, see: (a) Arundale, E.; Mikeska, L. A. Chem. Rev. 1952, 52, 505-555.
-
(1952)
Chem. Rev.
, vol.52
, pp. 505-555
-
-
Arundale, E.1
Mikeska, L.A.2
-
3
-
-
0001290261
-
-
Trost, B. M., Fleming, I., Heathcock, C. H., Eds.; Pergamon Press: New York
-
(c) Snider, B. B. In The Prins Reaction and Carbonyl Ene Reactions; Trost, B. M., Fleming, I., Heathcock, C. H., Eds.; Pergamon Press: New York, 1991; Vol. 2. pp 527-561.
-
(1991)
The Prins Reaction and Carbonyl Ene Reactions
, vol.2
, pp. 527-561
-
-
Snider, B.B.1
-
5
-
-
3242676775
-
-
For recent work on the Prins cyclization. see: (a) Yadav, K. V.; Kumar, N. V. J. Am. Chem. Soc. 2004, 126, 8652-8653.
-
(2004)
J. Am. Chem. Soc.
, vol.126
, pp. 8652-8653
-
-
Yadav, K.V.1
Kumar, N.V.2
-
8
-
-
0141743328
-
-
(d) Barry, C. S. J.; Crosby, S. R.; Harding, J. R.; Huges, R. A.; King, C. D.; Parker, G. D.; Willis, C. L. Org. Lett. 2003, 5, 2429-2432.
-
(2003)
Org. Lett.
, vol.5
, pp. 2429-2432
-
-
Barry, C.S.J.1
Crosby, S.R.2
Harding, J.R.3
Huges, R.A.4
King, C.D.5
Parker, G.D.6
Willis, C.L.7
-
9
-
-
0141629466
-
-
(e) Miranda, P. O.; Diaz, D. D.; Padron, J. I.; Bermejo, J.; Martin, V. S. Org. Lett. 2003, 5, 1979-1982.
-
(2003)
Org. Lett.
, vol.5
, pp. 1979-1982
-
-
Miranda, P.O.1
Diaz, D.D.2
Padron, J.I.3
Bermejo, J.4
Martin, V.S.5
-
10
-
-
0037165687
-
-
(f) Lopez, F.; Castedo, L.; Mascarenas, J. L. J. Am. Chem. Soc. 2002, 124, 4218-4219.
-
(2002)
J. Am. Chem. Soc.
, vol.124
, pp. 4218-4219
-
-
Lopez, F.1
Castedo, L.2
Mascarenas, J.L.3
-
11
-
-
0037015436
-
-
(g) Crosby, S. R.; Harding, J. R.; King, C. D.; Parker, G. D.; Willis, C. L. Org. Lett. 2002, 4, 3407-3410.
-
(2002)
Org. Lett.
, vol.4
, pp. 3407-3410
-
-
Crosby, S.R.1
Harding, J.R.2
King, C.D.3
Parker, G.D.4
Willis, C.L.5
-
12
-
-
0001134456
-
-
(h) Crosby, S. R.; Harding, J. R.; King, C. D.; Parker, G. D.; Willis, C. L. Org. Lett. 2002, 4, 577-580.
-
(2002)
Org. Lett.
, vol.4
, pp. 577-580
-
-
Crosby, S.R.1
Harding, J.R.2
King, C.D.3
Parker, G.D.4
Willis, C.L.5
-
13
-
-
0013154464
-
-
(i) Cho, Y. S.; Kim, H. Y.; Cha, J. H.; Pae, A. N.; Koh, H. Y.; Choi, J. H.; Chang, M. H. Org. Lett. 2002, 4, 2025-2028.
-
(2002)
Org. Lett.
, vol.4
, pp. 2025-2028
-
-
Cho, Y.S.1
Kim, H.Y.2
Cha, J.H.3
Pae, A.N.4
Koh, H.Y.5
Choi, J.H.6
Chang, M.H.7
-
14
-
-
0028360370
-
-
(a) Lolkema, L. D. M.; Semeyn, C.; Ashek, L.; Hiemstra, H.; Speckamp, W. N. Tetrahedron 1994, 50, 7129-7140.
-
(1994)
Tetrahedron
, vol.50
, pp. 7129-7140
-
-
Lolkema, L.D.M.1
Semeyn, C.2
Ashek, L.3
Hiemstra, H.4
Speckamp, W.N.5
-
16
-
-
0035891722
-
-
(c) Rychnovsky, S. D.; Marumoto, S.; Jaber, J. J. Org. Lett. 2001, 3, 3815-3818.
-
(2001)
Org. Lett.
, vol.3
, pp. 3815-3818
-
-
Rychnovsky, S.D.1
Marumoto, S.2
Jaber, J.J.3
-
17
-
-
0001134456
-
-
(d) Crosby, S. R.; Harding, J. R.; King, C. D.; Parker, G. D.; Willis, C. L. Org. Lett. 2002, 4, 577-580.
-
(2002)
Org. Lett.
, vol.4
, pp. 577-580
-
-
Crosby, S.R.1
Harding, J.R.2
King, C.D.3
Parker, G.D.4
Willis, C.L.5
-
18
-
-
0037015436
-
-
(e) Crosby, S. R.; Harding, J. R.; King, C. D.; Parker, G. D.; Willis, C. L. Org. Lett. 2002, 4, 3407-3410.
-
(2002)
Org. Lett.
, vol.4
, pp. 3407-3410
-
-
Crosby, S.R.1
Harding, J.R.2
King, C.D.3
Parker, G.D.4
Willis, C.L.5
-
20
-
-
0032496932
-
-
(a) Nokami, J.; Yoshizane, K.; Matsuura, H.; Sumida, S. I. J. Am. Chem. Soc. 1998, 120, 6609-6610.
-
(1998)
J. Am. Chem. Soc.
, vol.120
, pp. 6609-6610
-
-
Nokami, J.1
Yoshizane, K.2
Matsuura, H.3
Sumida, S.I.4
-
21
-
-
0033999235
-
-
(b) Sumida, S. I.; Ohga, M.; Mitani, J.; Nokami, J. J. Am. Chem. Soc. 2000, 122, 1310-1313.
-
(2000)
J. Am. Chem. Soc.
, vol.122
, pp. 1310-1313
-
-
Sumida, S.I.1
Ohga, M.2
Mitani, J.3
Nokami, J.4
-
22
-
-
0034802361
-
-
(c) Loh, T.-P.; Hu, Q.-Y.; Ma, L.-T. J. Am. Chem. Soc. 2001, 123, 2450-2451.
-
(2001)
J. Am. Chem. Soc.
, vol.123
, pp. 2450-2451
-
-
Loh, T.-P.1
Hu, Q.-Y.2
Ma, L.-T.3
-
23
-
-
0013282193
-
-
(d) Loh, T.-P.; Ken Lee, C.-L.; Tan, K.-T. Org. Lett. 2002, 4, 2985-2987.
-
(2002)
Org. Lett.
, vol.4
, pp. 2985-2987
-
-
Loh, T.-P.1
Ken Lee, C.-L.2
Tan, K.-T.3
-
24
-
-
0013319954
-
-
(e) Loh, T.-P.; Hu, Q.-Y.; Ma, L.-T. Org. Lett. 2002, 4, 2389-2391.
-
(2002)
Org. Lett.
, vol.4
, pp. 2389-2391
-
-
Loh, T.-P.1
Hu, Q.-Y.2
Ma, L.-T.3
-
25
-
-
2542422725
-
-
(f) Lee, C.-L. K.; Lee, C.-H. A.; Tan, K.-T.; Loh, T.-P. Org. Lett. 2004, 6, 1281-1283.
-
(2004)
Org. Lett.
, vol.6
, pp. 1281-1283
-
-
Lee, C.-L.K.1
Lee, C.-H.A.2
Tan, K.-T.3
Loh, T.-P.4
-
26
-
-
4344610661
-
-
For reviews on the Claisen and Cope rearrangements, see: (a) Martin Castro, A. M. Chem. Rev. 2004, 104, 2939-3002.
-
(2004)
Chem. Rev.
, vol.104
, pp. 2939-3002
-
-
Martin Castro, A.M.1
-
29
-
-
0037042279
-
-
Alder, R. W.; Harvey, J. N.; Oakley, M. T. J. Am. Chem. Soc. 2002, 124, 4960-4961.
-
(2002)
J. Am. Chem. Soc.
, vol.124
, pp. 4960-4961
-
-
Alder, R.W.1
Harvey, J.N.2
Oakley, M.T.3
-
30
-
-
0000527199
-
-
Cremer, D.; Gauss, J.; Chiles, R. F.; Blackburn, C. J. Am. Chem. Soc. 1985, 107, 2435-2441.
-
(1985)
J. Am. Chem. Soc.
, vol.107
, pp. 2435-2441
-
-
Cremer, D.1
Gauss, J.2
Chiles, R.F.3
Blackburn, C.4
-
31
-
-
4043069147
-
-
Jasti, R.; Vitale, J.; Rychnovsky, S. D. J. Am. Chem. Soc. 2004, 126, 9904-9905.
-
(2004)
J. Am. Chem. Soc.
, vol.126
, pp. 9904-9905
-
-
Jasti, R.1
Vitale, J.2
Rychnovsky, S.D.3
-
32
-
-
0003467672
-
-
John Wiley & Sons: New York
-
March, J. Advanced Organic Chemistry, 4th ed.; John Wiley & Sons: New York, 1992; p 782. "Those reactions are favored which involve the least change in atomic position and electronic configuration."
-
(1992)
Advanced Organic Chemistry, 4th Ed.
, pp. 782
-
-
March, J.1
-
33
-
-
0037151613
-
-
For a similar effect, see: Zhang, Y. D.; Reynolds, N. T.; Manju, K.; Rovis, T. J. Am. Chem. Soc. 2002, 124, 9720-9721.
-
(2002)
J. Am. Chem. Soc.
, vol.124
, pp. 9720-9721
-
-
Zhang, Y.D.1
Reynolds, N.T.2
Manju, K.3
Rovis, T.4
-
34
-
-
0035891722
-
-
Rychnovsky, S. D.; Marumoto, S.; Jaber, J. J. Org. Lett. 2001, 3, 3815-3818.
-
(2001)
Org. Lett.
, vol.3
, pp. 3815-3818
-
-
Rychnovsky, S.D.1
Marumoto, S.2
Jaber, J.J.3
-
38
-
-
0001488391
-
-
Keck, G. E.; Tarbet, K. H.; Geraci, L. S. J. Am. Chem. Soc. 1993, 115, 8467-8468.
-
(1993)
J. Am. Chem. Soc.
, vol.115
, pp. 8467-8468
-
-
Keck, G.E.1
Tarbet, K.H.2
Geraci, L.S.3
-
40
-
-
32744461058
-
-
note
-
A reviewer suggested a crossover experiment utilizing tetrabutylammonium chloride as a competitive nucleophile. We found that generation of a bromoether from acetoxy ether 25 at -60 °C followed by addition of tetrabutylammonium chloride and warming to 0 °C led to axial bromotetrahydropyran 27 in 83% ee. No chlorotetrahydropyrans were observed in the crude reaction mixture. This result is consistent with an ion-pairing argument in which recombination of a bromide anion from inside a solvent cage is faster than incorporation of a chloride anion from outside a solvent cage.
-
-
-
-
41
-
-
0029968191
-
-
Carbocations which are not highly stabilized are known to be quenched at a diffusional rate: (a) McCelland, R. A. Tetrahedron 1996, 52, 6823.
-
(1996)
Tetrahedron
, vol.52
, pp. 6823
-
-
McCelland, R.A.1
-
43
-
-
32744464183
-
-
note
-
20 Minima were characterized by their vibrational frequencies. Reported energies include unsealed zero-point corrections.
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