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1
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0032544469
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and references therein
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[1a] For a recent application to β-lactone synthesis, see: O. Dirat, C. Kouklovsky, Y. Langlois, J. Org. Chem. 1998, 63, 6634-6642 and references therein.
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Dirat, O.1
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0031955735
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[1b] For a review on oxazoline N-oxides [2 + 3] cycloadditions, see: Y. Langlois, Curr. Org. Chem. 1998, 2, 1-18.
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Langlois, Y.1
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3
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11544346529
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[1c] For a review on asymmetric 1,3-dipolar cycloadditions, see: K. V. Gothelf, K. A. Jorgensen, Chem. Rev. 1998, 98, 863-909.
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0021967315
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5
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0018173172
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G. Albers-Schönberg, B. H. Arison, O. D. Hensens, J. Hirshfield, K. Hoogsteen, E. A. Kaczka, R. E. Rhodes, J. S. Kahan, F. M. Kahan, R. W. Ratcliffe, E. Walton, L. J. Ruswinkle, R. B. Morin, B.G. Christensen, J. Am. Chem. Soc. 1978, 100, 6491-6499.
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Ruswinkle, L.J.12
Morin, R.B.13
Christensen, B.G.14
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7
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0032803170
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[4b] For a recent example of synthesis of β-methylcarbapenem using 3 as starting material, see: J.-C. Galland, S. Roland, J. Malpart, M. Savignac, J.-P. Genet, Eur. J. Org. Chem. 1999, 3, 621-626.
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Galland, J.-C.1
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Genet, J.-P.5
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8
-
-
85083140092
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-
note
-
The corresponding exo adduct has been isolated in 10% yield after chromatographic purification. NOE experiments allowed an unambiguous determination of the two asymmetric centres in both endo and exo adducts.
-
-
-
-
9
-
-
0031794248
-
-
and references therein
-
For a recent preparation of enamino esters, see: [6a] S. Fustero, M. G. de la Torre, V. Jofré, R. Pérez Carlon, A. Navarro, A. S. Fuentes, J. Org. Chem. 1998, 63, 8825-8836 and references therein. [6b] S. Fustero, M. D. Diaz, A. Navarro, E. Salavert, E. Aguilar. Tetrahedron Lett. 1999, 40, 1005-1008.
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Fustero, S.1
De La Torre, M.G.2
Jofré, V.3
Pérez Carlon, R.4
Navarro, A.5
Fuentes, A.S.6
-
10
-
-
0033613777
-
-
For a recent preparation of enamino esters, see: [6a] S. Fustero, M. G. de la Torre, V. Jofré, R. Pérez Carlon, A. Navarro, A. S. Fuentes, J. Org. Chem. 1998, 63, 8825-8836 and references therein. [6b] S. Fustero, M. D. Diaz, A. Navarro, E. Salavert, E. Aguilar. Tetrahedron Lett. 1999, 40, 1005-1008.
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Fustero, S.1
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Salavert, E.4
Aguilar, E.5
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11
-
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0001688963
-
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Blaise reaction: [7a] E. E. Blaise, C. R. Acad. Sci. 1901, 132, 478-480 and 978-980.
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C. R. Acad. Sci.
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Blaise, E.E.1
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12
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0001674261
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[7b] J. Cason, K. L. Rinehart Jr., S. D. Thornton Jr., J. Org. Chem. 1953, 18, 1594-1600.
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Cason, J.1
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15
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0031023976
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[7e] A. S.-Y. Lee, R.-Y. Cheng, O.-G. Pan, Tetrahedron Lett. 1997, 38, 443-446.
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Lee, A.S.-Y.1
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16
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0032513158
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[7f] J. Syed, S. Förster, F. Effenberger, Tetrahedron: Asymmetry 1998, 9, 805-815.
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Syed, J.1
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17
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85088332575
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-
note
-
[1]). A possible protonation of dipolarophile 11 can enhance the reactivity of this compound in a [3 + 2] cycloaddition. This point is still under investigation.
-
-
-
-
18
-
-
4043071644
-
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[9a] R. F. Borch, M. D. Bernstein, H. D. Durst, J. Am. Chem. Soc. 1971, 93, 2897-2904.
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Borch, R.F.1
Bernstein, M.D.2
Durst, H.D.3
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19
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85068666190
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[9b] For a review concerning the use of sodium cyanoborohydride, see: C. F. Lane, Synthesis 1975, 135-146.
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(1975)
Synthesis
, pp. 135-146
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-
Lane, C.F.1
-
20
-
-
85083138240
-
-
Configurations of the side chain in 12 were confirmed after further transformation into β-lactam 18
-
Configurations of the side chain in 12 were confirmed after further transformation into β-lactam 18.
-
-
-
-
21
-
-
85083126987
-
-
note
-
The selectivity of this reduction step is highly dependant on both temperature and solvents: at 0°C or in methanol a mixture of four isomers was obtained. A better selectivity was observed in the thienamycin series, vide infra.
-
-
-
-
23
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0028913777
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Ketol 15, isolated in 75% yield, can be transformed into hydroxylamino isoborneol and reused, see: T. Berranger, Y. Langlois, J. Org. Chem. 1995, 60, 1720-1726.
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(1995)
J. Org. Chem.
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Berranger, T.1
Langlois, Y.2
-
24
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0028559908
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H. Matsumura, Y. Nozaki, M. Sunagawa, Chem. Pharm. Bull. 1994, 42, 2467-2471.
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(1994)
Chem. Pharm. Bull.
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Matsumura, H.1
Nozaki, Y.2
Sunagawa, M.3
-
25
-
-
0028130028
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For a review concerning the stereoselective preparation of β-amino acids, see: D. C. Dole, Tetrahedron 1994, 50, 9517-9582.
-
(1994)
Tetrahedron
, vol.50
, pp. 9517-9582
-
-
Dole, D.C.1
-
26
-
-
85083147613
-
-
note
-
The value of the coupling constant C3H-C4H (J = 2.2 Hz) is characteristic for a trans relationship between these two hydrogens.
-
-
-
-
28
-
-
85088332722
-
-
note
-
3).
-
-
-
-
29
-
-
85088332260
-
-
note
-
3.
-
-
-
-
30
-
-
85083138464
-
-
note
-
With a cycloadduct substituted by a gem dimethyl group at C2, the diastereomer corresponding to compound 22b is the only product of the reaction. This result is also in agreement with a conformational restriction of the side chain due to hydrogen bonding in the iminium intermediate and a diastereoselective attack of hydride at the Re face of this iminium (unpublished work).
-
-
-
-
31
-
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0023830675
-
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[21a] M. Ihara, Takahashi, K. Fukumoto, T Kametani, J. Chem. Soc., Chem. Commun. 1988, 9-10.
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(1988)
J. Chem. Soc., Chem. Commun.
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Ihara, M.1
Takahashi2
Fukumoto, K.3
Kametani, T.4
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32
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-
37049085563
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[21b] M. Ihara, M. Takahashi, K. Fukumoto, T. Kametani, J. Chem. Soc., Perkin Trans. J 1989, 2215-2221.
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(1989)
J. Chem. Soc., Perkin Trans. J
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Ihara, M.1
Takahashi, M.2
Fukumoto, K.3
Kametani, T.4
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