-
1
-
-
0032500159
-
-
For a preliminary account of part of this work see: R. Lavilla, O. Coll, M. Nicolàs, J. Bosch, Tetrahedron Lett. 1998, 39, 5089-5092.
-
(1998)
Tetrahedron Lett.
, vol.39
, pp. 5089-5092
-
-
Lavilla, R.1
Coll, O.2
Nicolàs, M.3
Bosch, J.4
-
9
-
-
5844351514
-
-
M.-L. Bennasar, R. Lavilla, M. Alvarez, J. Bosch, Heterocycles 1988, 27, 789-824.
-
(1988)
Heterocycles
, vol.27
, pp. 789-824
-
-
Bennasar, M.-L.1
Lavilla, R.2
Alvarez, M.3
Bosch, J.4
-
10
-
-
0000390061
-
-
S. Goldmann, J. Stoltefuss, Angew. Chem. 1991, 103, 1587-1606; Angew. Chem. Int. Ed. Engl. 1991, 30, 1559-1578.
-
(1991)
Angew. Chem.
, vol.103
, pp. 1587-1606
-
-
Goldmann, S.1
Stoltefuss, J.2
-
11
-
-
0026342780
-
-
S. Goldmann, J. Stoltefuss, Angew. Chem. 1991, 103, 1587-1606; Angew. Chem. Int. Ed. Engl. 1991, 30, 1559-1578.
-
(1991)
Angew. Chem. Int. Ed. Engl.
, vol.30
, pp. 1559-1578
-
-
-
12
-
-
0001003164
-
-
[11a] R. Lavilla, F. Gullón, X. Barón, J. Bosch, Chem. Commun. 1997, 213-214.
-
(1997)
Chem. Commun.
, pp. 213-214
-
-
Lavilla, R.1
Gullón, F.2
Barón, X.3
Bosch, J.4
-
13
-
-
0032567316
-
-
[11b] R. Lavilla, X. Barón, O. Coll, F. Gullón, C. Masdeu, J. Bosch, J. Org. Chem. 1998, 63, 10001-10005.
-
(1998)
J. Org. Chem.
, vol.63
, pp. 10001-10005
-
-
Lavilla, R.1
Barón, X.2
Coll, O.3
Gullón, F.4
Masdeu, C.5
Bosch, J.6
-
14
-
-
0032556795
-
-
R. Lavilla, R. Kumar, O. Coll, C. Masdeu, J. Bosch, Chem. Commun. 1998, 2715-2716.
-
(1998)
Chem. Commun.
, pp. 2715-2716
-
-
Lavilla, R.1
Kumar, R.2
Coll, O.3
Masdeu, C.4
Bosch, J.5
-
15
-
-
0001007478
-
-
R. Lavilla, O. Coll, R. Kumar, J. Bosch, J. Org. Chem. 1998, 63, 2728-2730.
-
(1998)
J. Org. Chem.
, vol.63
, pp. 2728-2730
-
-
Lavilla, R.1
Coll, O.2
Kumar, R.3
Bosch, J.4
-
16
-
-
0024311265
-
-
M. E. Brewster, A. Simay, K. Czako, D. Winwood, H. Farag, N. Bodor, J. Org. Chem. 1989, 54, 3721-3726.
-
(1989)
J. Org. Chem.
, vol.54
, pp. 3721-3726
-
-
Brewster, M.E.1
Simay, A.2
Czako, K.3
Winwood, D.4
Farag, H.5
Bodor, N.6
-
17
-
-
0028047689
-
-
For the procedure, see: Y.-S. Wong, C. Marazano, D. Gnecco, B. C. Das, Tetrahedron Lett. 1994, 35, 707-710.
-
(1994)
Tetrahedron Lett.
, vol.35
, pp. 707-710
-
-
Wong, Y.-S.1
Marazano, C.2
Gnecco, D.3
Das, B.C.4
-
18
-
-
0000772498
-
-
Special care should be taken with hydroxy-substituted dihydropyridines 1a-c because of their propensity to undergo acid-catalysed cyclisation yielding the corresponding oxazolidines or oxazines. It is therefore advisable to use them immediately after preparation. For an account of this transformation with synthetic applications see: Y.-S. Wong, C. Marazano, D. Gnecco, Y. Génisson, A. Chiaroni, B.C. Das, J. Org. Chem. 1997, 62, 729-733.
-
(1997)
J. Org. Chem.
, vol.62
, pp. 729-733
-
-
Wong, Y.-S.1
Marazano, C.2
Gnecco, D.3
Génisson, Y.4
Chiaroni, A.5
Das, B.C.6
-
19
-
-
0003536850
-
-
Pergamon Press, Oxford, and references cited therein
-
See, for instance: P. Deslongchamps, Stereoelectronic Effects in Organic Chemistry, Pergamon Press, Oxford, 1983, p. 211-221, and references cited therein.
-
(1983)
Stereoelectronic Effects in Organic Chemistry
, pp. 211-221
-
-
Deslongchamps, P.1
-
20
-
-
0010426184
-
-
For representative examples, see: [18a] R. Amann, D. Spitzner, Angew. Chem. 1991, 103, 1373-1374; Angew. Chem. Int. Ed. Engl. 1991, 30, 1320-1321.
-
(1991)
Angew. Chem.
, vol.103
, pp. 1373-1374
-
-
Amann, R.1
Spitzner, D.2
-
21
-
-
0026051825
-
-
For representative examples, see: [18a] R. Amann, D. Spitzner, Angew. Chem. 1991, 103, 1373-1374; Angew. Chem. Int. Ed. Engl. 1991, 30, 1320-1321.
-
(1991)
Angew. Chem. Int. Ed. Engl.
, vol.30
, pp. 1320-1321
-
-
-
22
-
-
0028365355
-
-
[18b] P. Mangeney, R. Gosmini, S. Raussou, M. Commerçon, A. Alexakis, J. Org. Chem. 1994, 59, 1877-1888.
-
(1994)
J. Org. Chem.
, vol.59
, pp. 1877-1888
-
-
Mangeney, P.1
Gosmini, R.2
Raussou, S.3
Commerçon, M.4
Alexakis, A.5
-
23
-
-
0025897584
-
-
[18c] D. Gnecco, C. Marazano, B. C. Das, J. Chem. Soc., Chem. Commun. 1991, 625-626.
-
(1991)
J. Chem. Soc., Chem. Commun.
, pp. 625-626
-
-
Gnecco, D.1
Marazano, C.2
Das, B.C.3
-
24
-
-
0032572860
-
-
[18d] P. Mangeney, L. Hamon, S. Raussou, N. Urbain, A. Alexakis, Tetrahedron 1998, 54, 10349-10362.
-
(1998)
Tetrahedron
, vol.54
, pp. 10349-10362
-
-
Mangeney, P.1
Hamon, L.2
Raussou, S.3
Urbain, N.4
Alexakis, A.5
-
25
-
-
0028059761
-
-
[18e] D. L. Comins, S. P. Joseph, R. R. Goehring, J. Am. Chem. Soc. 1994, 116, 4719-4728.
-
(1994)
J. Am. Chem. Soc.
, vol.116
, pp. 4719-4728
-
-
Comins, D.L.1
Joseph, S.P.2
Goehring, R.R.3
-
26
-
-
0002942604
-
-
For a leading reference in the use of chiral 1,4-dihydropyridine equivalents see: M. Bonin, D. S. Grierson, J. Royer, H.-P. Husson, Organic Syntheses 1992, 70, 54-59.
-
(1992)
Organic Syntheses
, vol.70
, pp. 54-59
-
-
Bonin, M.1
Grierson, D.S.2
Royer, J.3
Husson, H.-P.4
-
27
-
-
0030996162
-
-
Fora recent example of an halocyclisation upon a chiral oxazolidine see: C. Agami, F. Couty, L. Hamon, O. Venier, J. Org. Chem. 1997, 62, 2106-2112.
-
(1997)
J. Org. Chem.
, vol.62
, pp. 2106-2112
-
-
Agami, C.1
Couty, F.2
Hamon, L.3
Venier, O.4
-
28
-
-
0001672360
-
-
E. Marcantoni, F. Nobili, G. Bartoli, M. Bosco, L. Sambri, J. Org. Chem. 1997, 62, 4183-4184.
-
(1997)
J. Org. Chem.
, vol.62
, pp. 4183-4184
-
-
Marcantoni, E.1
Nobili, F.2
Bartoli, G.3
Bosco, M.4
Sambri, L.5
-
29
-
-
0001046290
-
-
In phenylglycinol-derived oxazolopiperidines, the chemical shift of the hemiaminal proton in the NMR spectrum appears at lower field in the isomers which bear the phenyl group at the same face. For instance, see: J. Royer, H.-P. Husson, Heterocycles 1993, 36, 1493-1496.
-
(1993)
Heterocycles
, vol.36
, pp. 1493-1496
-
-
Royer, J.1
Husson, H.-P.2
-
30
-
-
0003417469
-
-
Ed.: B. M. Trost, Pergamon Press, Oxford, chapter 4.4
-
Although the indolizidine formation formally is a disfavoured process (5-endo-trig), several examples of this cyclisation are reported in the literature. For an excellent review see: L. E. Overman, D. J. Ricca in Comprehensive Organic Synthesis (Ed.: B. M. Trost), Pergamon Press, Oxford, 1991, vol. 2, chapter 4.4.
-
(1991)
Comprehensive Organic Synthesis
, vol.2
-
-
Overman, L.E.1
Ricca, D.J.2
-
31
-
-
85197329847
-
-
note
-
In MeOH solution no cyclisation took place, and the 3-iodo-2-methoxytetrahydropyridine was produced instead.
-
-
-
-
32
-
-
0027293731
-
-
For the intermolecular version of this transformation with N-acyl tetrahydropyridines see: Y. Matsumura, J. Terauchi, T. Yamamoto, T. Konno, T. Shono, Tetrahedron 1993, 49, 8503-8512.
-
(1993)
Tetrahedron
, vol.49
, pp. 8503-8512
-
-
Matsumura, Y.1
Terauchi, J.2
Yamamoto, T.3
Konno, T.4
Shono, T.5
-
33
-
-
0009494325
-
-
For instance, see: P. Scmitt, P. Melnyk, L. Demuynck, O. Bourde, J.-F. Pujol, C. Thal, Med. Chem. Res. 1993, 3, 24-33.
-
(1993)
Med. Chem. Res.
, vol.3
, pp. 24-33
-
-
Scmitt, P.1
Melnyk, P.2
Demuynck, L.3
Bourde, O.4
Pujol, J.-F.5
Thal, C.6
-
35
-
-
84982069605
-
-
[27b] H. Ernst, B. Hauser, E. Winterfeldt, Chem. Ber. 1981, 114, 1894-1906.
-
(1981)
Chem. Ber.
, vol.114
, pp. 1894-1906
-
-
Ernst, H.1
Hauser, B.2
Winterfeldt, E.3
-
36
-
-
0345217831
-
-
[27c] E. Vilsmaier, R. Adam, P. Altmeier, J. Fath, H.-J. Scherer, G. Maas, O. Wagner, Tetrahedron 1989, 45, 6683-6696.
-
(1989)
Tetrahedron
, vol.45
, pp. 6683-6696
-
-
Vilsmaier, E.1
Adam, R.2
Altmeier, P.3
Fath, J.4
Scherer, H.-J.5
Maas, G.6
Wagner, O.7
-
37
-
-
0023270476
-
-
For related structures, see: [27d] K. Hakam, M. Thielmann, T. Thielmann, E. Winterfeldt, Tetrahedron 1987, 43, 2035-2044.
-
(1987)
Tetrahedron
, vol.43
, pp. 2035-2044
-
-
Hakam, K.1
Thielmann, M.2
Thielmann, T.3
Winterfeldt, E.4
-
39
-
-
0345217830
-
-
Ed.: L. A. Paquette, Wiley, Chichester
-
Although reduction of the organic halide is an undesired side process on Zn-mediated conjugate additions (see for instance ref [18d]) the method has wide applicability: P. Knochel in Encyclopedia of Reagents for Organic Synthesis (Ed.: L. A. Paquette), Wiley, Chichester, 1995, vol. 8, p.5526.
-
(1995)
Encyclopedia of Reagents for Organic Synthesis
, vol.8
, pp. 5526
-
-
Knochel, P.1
-
41
-
-
0042789931
-
-
[30a] For a review on the radical-mediated ring-expansions (and ring-contractions), see: P. Dowd, W. Zhang, Chem. Rev. 1993, 93, 2091-2115.
-
(1993)
Chem. Rev.
, vol.93
, pp. 2091-2115
-
-
Dowd, P.1
Zhang, W.2
-
42
-
-
85197323650
-
-
note
-
[30b] The corresponding reduced cyclopropane analogue was not detected, which reflects the eagerness of cyclopropylcarbinyl radicals to undergo ring opening; for recent results in the field see:
-
-
-
-
43
-
-
0032514858
-
-
[30c] S.-Y. Choi, P. H. Toy, M. Newcomb, J. Org. Chem. 1998, 63, 8609-8613.
-
(1998)
J. Org. Chem.
, vol.63
, pp. 8609-8613
-
-
Choi, S.-Y.1
Toy, P.H.2
Newcomb, M.3
-
44
-
-
0033593265
-
-
[30d] E. J. Kantorowski, S. W. E. Eisenberg, W. H. Fink, M. J. Kurth, J. Org. Chem. 1999, 64, 570-580.
-
(1999)
J. Org. Chem.
, vol.64
, pp. 570-580
-
-
Kantorowski, E.J.1
Eisenberg, S.W.E.2
Fink, W.H.3
Kurth, M.J.4
-
45
-
-
0003136663
-
-
For related structures see: E. Wenkert, P. D. R. Moeller, Y.-J. Shi, J. Org. Chem. 1988, 53, 2383-2386.
-
(1988)
J. Org. Chem.
, vol.53
, pp. 2383-2386
-
-
Wenkert, E.1
Moeller, P.D.R.2
Shi, Y.-J.3
-
46
-
-
0000784885
-
-
Ed.: A.-u-Rahman, Elsevier, Amsterdam
-
For a review on these natural products, see: G. W. Gribble in Studies in Natural Product Chemistry, Stereoselective Synthesis (Part A) (Ed.: A.-u-Rahman), Elsevier, Amsterdam, 1988, vol. 1. p. 123-162.
-
(1988)
Studies in Natural Product Chemistry, Stereoselective Synthesis (Part A)
, vol.1
, pp. 123-162
-
-
Gribble, G.W.1
-
47
-
-
37049109374
-
-
For recent syntheses of these alkaloids, see: [33a] I. Ninomiya, Y. Tada, T. Kiguchi, O. Yamamoto, T. Naito, J. Chem. Soc., Perkin Trans. 1 1984, 2035-2038.
-
(1984)
J. Chem. Soc., Perkin Trans. 1
, pp. 2035-2038
-
-
Ninomiya, I.1
Tada, Y.2
Kiguchi, T.3
Yamamoto, O.4
Naito, T.5
-
48
-
-
0345649676
-
-
[33b] P. J. Sankar, S. K. Das, V. S. Giri, Heterocycles 1991, 32, 1109-1116.
-
(1991)
Heterocycles
, vol.32
, pp. 1109-1116
-
-
Sankar, P.J.1
Das, S.K.2
Giri, V.S.3
-
51
-
-
0007983335
-
-
M. Lounasmaa, P. Hanhinen, S. Lipponen, Heterocycles 1996, 43, 1365-1370.
-
(1996)
Heterocycles
, vol.43
, pp. 1365-1370
-
-
Lounasmaa, M.1
Hanhinen, P.2
Lipponen, S.3
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