-
1
-
-
0027401155
-
-
Reviews: a
-
Reviews: a) Zimmer R.: Synthesis 1993, 165;
-
(1993)
Synthesis
, vol.165
-
-
Zimmer, R.1
-
3
-
-
0034245863
-
-
Zimmer R., Dinesh C. U., Nandanan E., Khan F. A.: Chem. Rev. 2000, 100, 3067;
-
(2000)
Chem. Rev.
, vol.100
, pp. 3067
-
-
Zimmer, R.1
Dinesh, C.U.2
Nandanan, E.3
Khan, F.A.4
-
5
-
-
4644273297
-
-
N. Krause and A. S. K. Hashmi, Eds, Wiley-VCH, Weinheim
-
Zimmer R., Reissig H.-U. in: Modern Allene Chemistry (N. Krause and A. S. K. Hashmi, Eds), p. 425. Wiley-VCH, Weinheim 2004;
-
(2004)
Modern Allene Chemistry
, pp. 425
-
-
Zimmer, R.1
Reissig, H.-U.2
-
7
-
-
49649103604
-
-
N. Krause, Ed., Thieme, Stuttgart
-
Reissig H.-U., Zimmer R. in: Science of Synthesis (N. Krause, Ed.), Vol. 44, p. 301. Thieme, Stuttgart 2007;
-
(2007)
Science of Synthesis
, vol.44
, pp. 301
-
-
Reissig, H.-U.1
Zimmer, R.2
-
11
-
-
0000871194
-
-
Gange D., Magnus P., Bass L., Arnold E. V., Clardy J.: J. Am. Chem. Soc. 1980, 102, 2134;
-
(1980)
J. Am. Chem. Soc.
, vol.102
, pp. 2134
-
-
Gange, D.1
Magnus, P.2
Bass, L.3
Arnold, E.V.4
Clardy, J.5
-
16
-
-
0035354662
-
-
Wong Y.-S., Trân-Huu-Dâu M.-E., Wartchow R., Winterfeldt E.: Chem. Eur. J. 2001, 7, 2349;
-
(2001)
Chem. Eur. J.
, vol.7
, pp. 2349
-
-
Wong, Y.-S.1
Trân-Huu-Dâu, M.-E.2
Wartchow, R.3
Winterfeldt, E.4
-
19
-
-
0032537166
-
-
a) Nedolya N. A., Brandsma L., Tarasova O. A., Verkruijsse H. D., Trofimov B. A.: Tetrahedron Lett. 1998, 39, 2409;
-
(1998)
Tetrahedron Lett.
, vol.39
, pp. 2409
-
-
Nedolya, N.A.1
Brandsma, L.2
Tarasova, O.A.3
Verkruijsse, H.D.4
Trofimov, B.A.5
-
24
-
-
0344838588
-
-
a) Flögel O., Okala Amombo M. G., Reissig H.-U., Zahn G., Brüdgam I., Hartl H.: Chem. Eur. J. 2003, 9, 1405;
-
(2003)
Chem. Eur. J.
, vol.9
, pp. 1405
-
-
Flögel, O.1
Amombo, M.G.O.2
Reissig, H.-U.3
Zahn, G.4
Brüdgam, I.5
Hartl, H.6
-
31
-
-
16244405908
-
-
Helms M., Schade W., Pulz R., Watanabe T., Al-Harrasi A., Fišera L., Hlobilová I., Zahn G., Reissig H.-U.: Eur. J. Org. Chem. 2005, 1003.
-
(2005)
Eur. J. Org. Chem.
, pp. 1003
-
-
Helms, M.1
Schade, W.2
Pulz, R.3
Watanabe, T.4
Al-Harrasi, A.5
Fišera, L.6
Hlobilová, I.7
Zahn, G.8
Reissig, H.-U.9
-
36
-
-
38849106858
-
-
Bressel B., Egart B., Al-Harrasi A., Pulz R., Reissig H.-U., Brüdgam I.: Eur. J. Org. Chem. 2008, 467;
-
(2008)
Eur. J. Org. Chem.
, vol.467
-
-
Bressel, B.1
Egart, B.2
Al-Harrasi, A.3
Pulz, R.4
Reissig, H.-U.5
Brüdgam, I.6
-
40
-
-
0001806627
-
-
Reviews: a, in:, A. Hassner, Ed., Part, Wiley, New York
-
Reviews: a) Deyrup J. A. in: The Chemistry of Heterocyclic Compounds (A. Hassner, Ed.), Vol. 42, Part 1, p. 1. Wiley, New York 1983;
-
(1983)
The Chemistry of Heterocyclic Compounds
, vol.42
, Issue.1
, pp. 1
-
-
Deyrup, J.A.1
-
43
-
-
0000400367
-
-
For ring-opening reactions of aziridine derivatives, see: d
-
For ring-opening reactions of aziridine derivatives, see: d) Tanner D.: Angew. Chem. 1994, 105, 625;
-
(1994)
Angew. Chem.
, vol.105
, pp. 625
-
-
Tanner, D.1
-
46
-
-
0029918287
-
-
a) Khim S.-K., Cederstrom E., Ferri D. C., Mariano P. S.: Tetrahedron 1996, 52, 3195;
-
(1996)
Tetrahedron
, vol.52
, pp. 3195
-
-
Khim, S.-K.1
Cederstrom, E.2
Ferri, D.C.3
Mariano, P.S.4
-
49
-
-
72149104484
-
-
3 indicates that 4 is essentially enantiopure. It is very likely that the corresponding lithiated aziridine derivative does not undergo inversion of configuration
-
3) indicates that 4 is essentially enantiopure. It is very likely that the corresponding lithiated aziridine derivative does not undergo inversion of configuration
-
-
-
-
50
-
-
42149123402
-
-
see:, before the presumably very fast intramolecular addition to the activated benzene ring
-
(see: Capriati V., Florio S., Luisi R., Mazzanti A., Musio B.: J. Org. Chem. 2008, 73, 3197) before the presumably very fast intramolecular addition to the activated benzene ring.
-
(2008)
J. Org. Chem.
, vol.73
, pp. 3197
-
-
Capriati, V.1
Florio, S.2
Luisi, R.3
Mazzanti, A.4
Musio, B.5
-
51
-
-
0026036123
-
-
For formation of 4 in racemic form, see
-
a) For formation of 4 in racemic form, see: Breternitz H. J., Schaumann E., Adiwidjaja G.: Tetrahedron Lett. 1991, 32, 1299;
-
(1991)
Tetrahedron Lett.
, vol.32
, pp. 1299
-
-
Breternitz, H.J.1
Schaumann, E.2
Adiwidjaja, G.3
-
52
-
-
0037023469
-
-
for a similar compound, see: b
-
for a similar compound, see: b) Aggarwal V. K., Alonso E., Ferrara M., Spey S. E.: J. Org. Chem. 2002, 67, 2335.
-
(2002)
J. Org. Chem.
, vol.67
, pp. 2335
-
-
Aggarwal, V.K.1
Alonso, E.2
Ferrara, M.3
Spey, S.E.4
-
53
-
-
51249100498
-
-
Most recent comprehensive reviews: a
-
Most recent comprehensive reviews: a) Arcadi A.: Chem. Rev. 2008, 108, 3266;
-
(2008)
Chem. Rev.
, vol.108
, pp. 3266
-
-
Arcadi, A.1
-
56
-
-
72149126765
-
-
2a-2g for the formation of dihydrofuran derivatives; other solvents did not allow this transformation, see:, Freie Universität Berlin, Berlin
-
2a-2g for the formation of dihydrofuran derivatives); other solvents did not allow this transformation, see: Prisyazhnyuk V.: Ph. D. Thesis. Freie Universität Berlin, Berlin 2007.
-
(2007)
-
-
Prisyazhnyuk, V.1
-
57
-
-
72149126299
-
-
25. CCDC 720141 contains the supplementary crystallographic data for this paper. These data can be obtained free of charge via, or from the Cambridge Crystallographic Data Centre, 12, Union Road, Cambridge, CB2 1EZ, UK; fax: +44 1223 336033; or deposit@ccdc.cam.ac.uk
-
25. CCDC 720141 contains the supplementary crystallographic data for this paper. These data can be obtained free of charge via www.ccdc.cam.ac.uk /conts/retrieving.html (or from the Cambridge Crystallographic Data Centre, 12, Union Road, Cambridge, CB2 1EZ, UK; fax: +44 1223 336033; or deposit@ccdc.cam.ac.uk).
-
-
-
-
58
-
-
34247620478
-
-
This rearrangement may be caused by excess lithiated methoxyallene present or its presumed thermal decomposition product lithium methoxide. The process requires deprotonation at the terminal allene carbon and reprotonation in position 3 to generate the alkyne moiety. The overall driving force could be the subsequent deprotonation of the fairly acidic alkyne proton to afford the dianions of compounds 6. The fairly low yields indicate that considerable decomposition is occurring under these reaction conditions. For the formation of similar compounds by an alternative approach, see
-
This rearrangement may be caused by excess lithiated methoxyallene present or its presumed thermal decomposition product lithium methoxide. The process requires deprotonation at the terminal allene carbon and reprotonation in position 3 to generate the alkyne moiety. The overall driving force could be the subsequent deprotonation of the fairly acidic alkyne proton to afford the dianions of compounds 6. The fairly low yields indicate that considerable decomposition is occurring under these reaction conditions. For the formation of similar compounds by an alternative approach, see: Alouane N., Vrancken E., Mangeney P.: Synthesis 2007, 1261.
-
(2007)
Synthesis
, pp. 1261
-
-
Alouane, N.1
Vrancken, E.2
Mangeney, P.3
-
59
-
-
0001608555
-
-
For a related cyclization with toluenesulfonic acid, see
-
For a related cyclization with toluenesulfonic acid, see: Goldstein S. W., Overman L. E., Rabinowitz M. H.: J. Org. Chem. 1992, 57, 1179.
-
(1992)
J. Org. Chem.
, vol.57
, pp. 1179
-
-
Goldstein, S.W.1
Overman, L.E.2
Rabinowitz, M.H.3
-
60
-
-
0001675894
-
-
For examples of NBS, NIS or iodine-promoted cyclizations of allenyl alcohols to dihydrofuran derivatives, see: a
-
For examples of NBS, NIS or iodine-promoted cyclizations of allenyl alcohols to dihydrofuran derivatives, see: a) Marshall J. A., Wang X.-J.: J. Org. Chem. 1990, 55, 2995;
-
(1990)
J. Org. Chem.
, vol.55
, pp. 2995
-
-
Marshall, J.A.1
Wang, X.-J.2
-
62
-
-
53149119995
-
-
Li J., Fu C., Chen G., Chai G., Ma S.: Adv. Synth. Catal. 2008, 350, 1376.
-
(2008)
Adv. Synth. Catal.
, vol.350
, pp. 1376
-
-
Li, J.1
Fu, C.2
Chen, G.3
Chai, G.4
Ma, S.5
-
63
-
-
0001044552
-
-
a) Ballestri M., Chatgilialogulo C., Clark K. B., Griller D., Giese B., Kopping B.: J. Org. Chem. 1991, 56, 678;
-
(1991)
J. Org. Chem.
, vol.56
, pp. 678
-
-
Ballestri, M.1
Chatgilialogulo, C.2
Clark, K.B.3
Griller, D.4
Giese, B.5
Kopping, B.6
-
66
-
-
36448986007
-
-
For the importance of this type of compounds, see: a
-
For the importance of this type of compounds, see: a) Satyanarayana G., Maier M. E.: Tetrahedron 2008, 64, 356;
-
(2008)
Tetrahedron
, vol.64
, pp. 356
-
-
Satyanarayana, G.1
Maier, M.E.2
-
67
-
-
48849117471
-
-
references therein
-
Yang X., Zhai H., Li Z.: Org. Lett. 2008, 10, 2457, and references therein.
-
(2008)
Org. Lett.
, vol.10
, pp. 2457
-
-
Yang, X.1
Zhai, H.2
Li, Z.3
-
68
-
-
84981751304
-
The cyclization to 9 was performed under Grewe-type cyclization conditions
-
The cyclization to 9 was performed under Grewe-type cyclization conditions: a) Grewe R., Mondon A.: Ber. Dtsch. Chem. Ges. 1948, 81, 279;
-
(1948)
Ber. Dtsch. Chem. Ges.
, vol.81
, pp. 279
-
-
Grewe, R.1
Mondon, A.2
-
72
-
-
0034861316
-
-
Langler R. F., Raheja R. K., Schank K., Beck H.: Helv. Chim. Acta 2001, 84, 1943;
-
(2001)
Helv. Chim. Acta
, vol.84
, pp. 1943
-
-
Langler, R.F.1
Raheja, R.K.2
Schank, K.3
Beck, H.4
-
74
-
-
72149135076
-
-
3b
-
3b.
-
-
-
-
75
-
-
0001728892
-
-
For a review concerning Umpolung of reactivity, see
-
For a review concerning Umpolung of reactivity, see: Seebach D.: Angew. Chem. 1979, 91, 259;
-
(1979)
Angew. Chem.
, vol.91
, pp. 259
-
-
Seebach, D.1
-
77
-
-
0033709712
-
-
For recent reviews on the stereoselective preparation of piperidine derivatives, see: a
-
For recent reviews on the stereoselective preparation of piperidine derivatives, see: a) Laschat S., Dickner T.: Synthesis 2000, 1781;
-
(2000)
Synthesis
, pp. 1781
-
-
Laschat, S.1
Dickner, T.2
-
78
-
-
0037459890
-
-
Weintraub P. M., Sabol J. S., Kane J. M., Borcherding D. R.: Tetrahedron 2003, 59, 2953;
-
(2003)
Tetrahedron
, vol.59
, pp. 2953
-
-
Weintraub, P.M.1
Sabol, J.S.2
Kane, J.M.3
Borcherding, D.R.4
-
81
-
-
20844458768
-
-
for selected original reports, see: e
-
for selected original reports, see: e) Ouchi H., Mihara Y., Takahata H.: J. Org. Chem. 2005, 70, 5207;
-
(2005)
J. Org. Chem.
, vol.70
, pp. 5207
-
-
Ouchi, H.1
Mihara, Y.2
Takahata, H.3
|