-
1
-
-
46549103031
-
-
For reviews on N-acyliminium ion chemistry, see: (a) Speckamp, W. N.; Hiemstra, H. Tetrahedron 1985, 41, 4367-4416.
-
(1985)
Tetrahedron
, vol.41
, pp. 4367-4416
-
-
Speckamp, W.N.1
Hiemstra, H.2
-
2
-
-
77957077000
-
-
Brossi, A., Ed.; Academic Press: New York
-
(b) Hiemstra, H.; Speckamp, W. N. In The Alkaloids; Brossi, A., Ed.; Academic Press: New York, 1988; Vol. 32, pp 271-339.
-
(1988)
The Alkaloids
, vol.32
, pp. 271-339
-
-
Hiemstra, H.1
Speckamp, W.N.2
-
3
-
-
0001673091
-
-
Trost, B. M., Fleming, I., Eds.; Pergamon Press: Oxford
-
(c) Hiemstra, H.; Speckamp, W. N. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon Press: Oxford, 1991; Vol. 2, pp 1047-1082.
-
(1991)
Comprehensive Organic Synthesis
, vol.2
, pp. 1047-1082
-
-
Hiemstra, H.1
Speckamp, W.N.2
-
4
-
-
0001513757
-
-
Helmchen, G., Hoffmann, R. W., Muzler, J., Schaumann, E., Eds.; Thieme: Stuttgart, Workbench ed. E21
-
(d) de Koning, H.; Speckamp, W. N. In Stereoselective Synthesis [Houben-Weyl]; Helmchen, G., Hoffmann, R. W., Muzler, J., Schaumann, E., Eds.; Thieme: Stuttgart, 1996; Workbench ed. E21, Vol. 3, pp 1952-2010.
-
(1996)
Stereoselective Synthesis [Houben-Weyl]
, vol.3
, pp. 1952-2010
-
-
De Koning, H.1
Speckamp, W.N.2
-
6
-
-
2942574530
-
-
(f) Royer, J.; Bonin, M.; Micouin, L. Chem. Rev. 2004, 104, 2311-2352.
-
(2004)
Chem. Rev.
, vol.104
, pp. 2311-2352
-
-
Royer, J.1
Bonin, M.2
Micouin, L.3
-
7
-
-
1842430777
-
-
(g) Maryanoff, B. E.; Zhang, H.-C.; Cohen, J. H.; Turchi, I. J.; Maryanoff, C. A. Chem. Rev. 2004, 104, 1431-1628.
-
(2004)
Chem. Rev.
, vol.104
, pp. 1431-1628
-
-
Maryanoff, B.E.1
Zhang, H.-C.2
Cohen, J.H.3
Turchi, I.J.4
Maryanoff, C.A.5
-
8
-
-
84906288269
-
-
Katritzky, A. R., Taylor, R. J. K., Eds.; Elsevier: Oxford
-
(h) Dobbs, A. P.; Rossiter, S. In Comprehensive Organic Functional Group Transformations II; Katritzky, A. R., Taylor, R. J. K., Eds.; Elsevier: Oxford, 2005; Vol. 3, pp 419-450.
-
(2005)
Comprehensive Organic Functional Group Transformations II
, vol.3
, pp. 419-450
-
-
Dobbs, A.P.1
Rossiter, S.2
-
9
-
-
0033986185
-
-
For reviews, see ref 1. For some selected examples of diastereoselective intramolecular α-amidoalkylation reactions of cyclic N-acyliminium ions, see the following references. Steric control by the substituents in the ring: (a) Ostendorf, M.; van der Neut, S.; Rutjes, F. P. J. T.; Hiemstra, H. Eur. J. Org. Chem. 2000, 65, 115-124.
-
(2000)
Eur. J. Org. Chem.
, vol.65
, pp. 115-124
-
-
Ostendorf, M.1
Van Der Neut, S.2
Rutjes, F.P.J.T.3
Hiemstra, H.4
-
10
-
-
0035066574
-
-
(b) Consonni, A.; Danieli, B.; Lesma, G.; Passarella, D.; Piacenti, P.; Silvani, A. Eur. J. Org. Chem. 2001, 66, 1377-1383.
-
(2001)
Eur. J. Org. Chem.
, vol.66
, pp. 1377-1383
-
-
Consonni, A.1
Danieli, B.2
Lesma, G.3
Passarella, D.4
Piacenti, P.5
Silvani, A.6
-
11
-
-
0036323436
-
-
(c) Hwang, D. J.; Kang, S. S.; Lee, J. Y.; Choi, J. H.; Park, H.; Lee, Y. S. Synth. Commun. 2002, 32, 2499-2505.
-
(2002)
Synth. Commun.
, vol.32
, pp. 2499-2505
-
-
Hwang, D.J.1
Kang, S.S.2
Lee, J.Y.3
Choi, J.H.4
Park, H.5
Lee, Y.S.6
-
14
-
-
3142746067
-
-
(f) Mostowicz, D.; Wójcik, R.; Dolega, G.; Kahuza, Z. Tetrahedron Lett. 2004, 45, 6011-6015.
-
(2004)
Tetrahedron Lett
, vol.45
, pp. 6011-6015
-
-
Mostowicz, D.1
Wójcik, R.2
Dolega, G.3
Kahuza, Z.4
-
15
-
-
14344264454
-
-
(g) Siwicka, A.; Wojasiewicz, K.; Rosiek, B.; Leniewski, A.; Maurin, J. K.; Czarnocki, Z. Tetrahedron: Asymmetry 2005, 16, 975-993.
-
(2005)
Tetrahedron: Asymmetry
, vol.16
, pp. 975-993
-
-
Siwicka, A.1
Wojasiewicz, K.2
Rosiek, B.3
Leniewski, A.4
Maurin, J.K.5
Czarnocki, Z.6
-
16
-
-
20844431887
-
-
(h) Hanessian, S.; Tremblay, M.; Marzi, M.; del Valle, J. R. J. Org. Chem. 2005, 70, 5070-5085.
-
(2005)
J. Org. Chem.
, vol.70
, pp. 5070-5085
-
-
Hanessian, S.1
Tremblay, M.2
Marzi, M.3
Del Valle, J.R.4
-
17
-
-
0034743059
-
-
Steric control by the substituents along the chain connecting the π-nucleophiles and the nitrogen atom: (i) Bahajaj, A. A.; Vernon, J. M.; Wilson, G. D. J. Chem. Soc., Perkin Trans. 1 2001, 1446-1451.
-
(2001)
J. Chem. Soc., Perkin Trans. 1
, pp. 1446-1451
-
-
Bahajaj, A.A.1
Vernon, J.M.2
Wilson, G.D.3
-
18
-
-
0035847191
-
-
(j) Katritzky, A. R.; Mehta, S.; He, H.-Y. J. Org. Chem. 2001, 66, 148-152.
-
(2001)
J. Org. Chem.
, vol.66
, pp. 148-152
-
-
Katritzky, A.R.1
Mehta, S.2
He, H.-Y.3
-
20
-
-
0141922089
-
-
(l) Ardeo, A.; García, E.; Arrasate, S.; Lete, E.; Sotomayor, N. Tetrahedron Lett. 2003, 44, 8445-8448.
-
(2003)
Tetrahedron Lett
, vol.44
, pp. 8445-8448
-
-
Ardeo, A.1
García, E.2
Arrasate, S.3
Lete, E.4
Sotomayor, N.5
-
21
-
-
85022430382
-
-
(a) Lete, E.; Egiarte, A.; Sotomayor, N.; Vicente, T.; Villa, M. J. Synlett 1993, 41-42.
-
(1993)
Synlett
, pp. 41-42
-
-
Lete, E.1
Egiarte, A.2
Sotomayor, N.3
Vicente, T.4
Villa, M.J.5
-
22
-
-
0028902813
-
-
(b) Collado, M. I.; Lete, E.; Sotomayor, N.; Villa, M. J. Tetrahedron 1995, 51, 4701-4710.
-
(1995)
Tetrahedron
, vol.51
, pp. 4701-4710
-
-
Collado, M.I.1
Lete, E.2
Sotomayor, N.3
Villa, M.J.4
-
23
-
-
0030593585
-
-
(c) Collado, M. I.; Sotomayor, N.; Villa, M. J.; Lete, E. Tetrahedron Lett. 1996, 37, 6193-6196.
-
(1996)
Tetrahedron Lett
, vol.37
, pp. 6193-6196
-
-
Collado, M.I.1
Sotomayor, N.2
Villa, M.J.3
Lete, E.4
-
24
-
-
0001157440
-
-
(d) Collado, M. I.; Manteca, I.; Sotomayor, N.; Villa, M. J.; Lete, E. J. Org. Chem. 1997, 62, 2080-2092.
-
(1997)
J. Org. Chem.
, vol.62
, pp. 2080-2092
-
-
Collado, M.I.1
Manteca, I.2
Sotomayor, N.3
Villa, M.J.4
Lete, E.5
-
25
-
-
0141972707
-
-
(e) Osante, I.; García, E.; Ardeo, A.; Arrasate, S.; Lete, E.; Sotomayor, N. Recent Res. Dev. Org. Chem. 2002, 8, 103-111.
-
(2002)
Recent Res. Dev. Org. Chem.
, vol.8
, pp. 103-111
-
-
Osante, I.1
García, E.2
Ardeo, A.3
Arrasate, S.4
Lete, E.5
Sotomayor, N.6
-
26
-
-
0033958882
-
-
(a) Osante, I.; Collado, M. I.; Lete, E.; Sotomayor, N. Synlett 2000, 101-103.
-
(2000)
Synlett
, pp. 101-103
-
-
Osante, I.1
Collado, M.I.2
Lete, E.3
Sotomayor, N.4
-
27
-
-
0035072554
-
-
(b) Osante, I.; Collado, M. I.; Lete, E.; Sotomayor, N. Eur. J. Org. Chem. 2001, 1267-1277.
-
(2001)
Eur. J. Org. Chem.
, pp. 1267-1277
-
-
Osante, I.1
Collado, M.I.2
Lete, E.3
Sotomayor, N.4
-
29
-
-
2442705392
-
-
(b) González-Temprano, I.; Osante, I.; Sotomayor, N.; Lete, E. J. Org. Chem. 2004, 69, 3875-3885.
-
(2004)
J. Org. Chem.
, vol.69
, pp. 3875-3885
-
-
González-Temprano, I.1
Osante, I.2
Sotomayor, N.3
Lete, E.4
-
30
-
-
0035911014
-
-
García, E.; Arrasate, S.; Ardeo, A.; Lete, E.; Sotomayor, N. Tetrahedron Lett. 2001, 42, 1511-1513.
-
(2001)
Tetrahedron Lett
, vol.42
, pp. 1511-1513
-
-
García, E.1
Arrasate, S.2
Ardeo, A.3
Lete, E.4
Sotomayor, N.5
-
31
-
-
0035806297
-
-
(a) Allin, S. M.; James, S. L.; Martin, W. P.; Smith, T. A. D. Tetrahedron Lett. 2001, 42, 3943-3946.
-
(2001)
Tetrahedron Lett
, vol.42
, pp. 3943-3946
-
-
Allin, S.M.1
James, S.L.2
Martin, W.P.3
Smith, T.A.D.4
-
32
-
-
0034746883
-
-
(b) Allin, S. M.; James, S. L.; Martin, W. P.; Smith, T. A. D.; Elsegood, M. R. J. J. Chem. Soc., Parkin Trans. 1 2001, 3029-3036.
-
(2001)
J. Chem. Soc., Parkin Trans. 1
, pp. 3029-3036
-
-
Allin, S.M.1
James, S.L.2
Martin, W.P.3
Smith, T.A.D.4
Elsegood, M.R.J.5
-
33
-
-
2442698345
-
-
Transl. Khim. Geterotsikl. Soedin
-
Pyrrolo[2,1-a]isoquinolones have attracted considerable interest because they possess antidepressant, muscarinic agonist, antiplatelet, and anticancer activity. Moreover, they can be used as PET radiotracers for imaging serotonin uptake sites. The importance of these nitrogen heterocycles is further enhanced by their utility as advanced intermediates for the synthesis of alkaloids. For a general review on properties, synthesis, and reactivity of pyrrolo[2,1-a] isoquinolines, see: Mikhailovskii, A. G.; Shklyaev, V. S. Chem. Heterocycl. Compd. 1997, 33, 243-265; Transl. Khim. Geterotsikl. Soedin.
-
(1997)
Chem. Heterocycl. Compd.
, vol.33
, pp. 243-265
-
-
Mikhailovskii, A.G.1
Shklyaev, V.S.2
-
34
-
-
28744432715
-
-
note
-
O-Silylation of 4 was carried out with imidazole and TBDPSCl to give 5a in excellent yield (95%). However, the yields of the benzyl and methyl ethers 5b and 5c were only moderate due to the formation of side products 6 (35%) and 7 (30%), respectively. Several attempts to improve these yields failed. See Supporting Information.
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-
-
-
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-
-
0029919982
-
-
The use of 1, 2, or 3 equiv of MeLi led to lower yields of the oxoamides and starting material. The requirement of more than stoichiometric amounts of organolithiums has been attributed to coordination of the organolithium to oxygenated groups. See: Sardina, F. J.; Blanco, M. J. Org. Chem. 1996, 61, 4748-4755.
-
(1996)
J. Org. Chem.
, vol.61
, pp. 4748-4755
-
-
Sardina, F.J.1
Blanco, M.2
-
36
-
-
28744434072
-
-
note
-
All enantiomeric excesses were checked by chiral stationary phase HPLC by comparison with the corresponding racemates, obtained by analogous routes from racemic D,L-DOPA.
-
-
-
-
38
-
-
45249125690
-
-
Mooiveer, H.; Hiemstra, H.; Speckamp, W. N. Tetrahedron 1989, 45, 4627-4636.
-
(1989)
Tetrahedron
, vol.45
, pp. 4627-4636
-
-
Mooiveer, H.1
Hiemstra, H.2
Speckamp, W.N.3
-
39
-
-
0000116493
-
-
Maryanoff, B. E.; McComsey, D. F.; Duhl-Emswiler, B. A. J. Org. Chem. 1983, 48, 5062-5074.
-
(1983)
J. Org. Chem.
, vol.48
, pp. 5062-5074
-
-
Maryanoff, B.E.1
McComsey, D.F.2
Duhl-Emswiler, B.A.3
-
40
-
-
0028902813
-
-
Collado, M. I.; Lete, E.; Sotomayor, N.; Villa, M. J. Tetrahedron 1995, 51, 4701-4710.
-
(1995)
Tetrahedron
, vol.51
, pp. 4701-4710
-
-
Collado, M.I.1
Lete, E.2
Sotomayor, N.3
Villa, M.J.4
-
41
-
-
0033605165
-
-
Chalard, P.; Remuson, R.; Gelas-Mialhe, Y.; Gramain, J.-C.; Canet, I. Tetrahedron Lett. 1999, 40, 1661-1664.
-
(1999)
Tetrahedron Lett
, vol.40
, pp. 1661-1664
-
-
Chalard, P.1
Remuson, R.2
Gelas-Mialhe, Y.3
Gramain, J.-C.4
Canet, I.5
-
43
-
-
22244448384
-
-
Bassas, O.; Llor, N.; Santos, M. M. M.; Griera, R.; Molins, E.; Amat, M.; Bosch, J. Org. Lett. 2005, 7, 2817-2820.
-
(2005)
Org. Lett.
, vol.7
, pp. 2817-2820
-
-
Bassas, O.1
Llor, N.2
Santos, M.M.M.3
Griera, R.4
Molins, E.5
Amat, M.6
Bosch, J.7
-
44
-
-
0032474793
-
-
Allin, S. M.; Northfield, C. J.; Page, M. I.; Slawin, A. M. Z. Tetrahedron Lett. 1998, 39, 4905-4908.
-
(1998)
Tetrahedron Lett
, vol.39
, pp. 4905-4908
-
-
Allin, S.M.1
Northfield, C.J.2
Page, M.I.3
Slawin, A.M.Z.4
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