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1
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33748973610
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Part of the Dissertation (ETH No 11350) of Eidgenössische Technische Hochschule Zürich
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Part of the Dissertation (ETH No 11350) of O.B., Eidgenössische Technische Hochschule Zürich, 1995.
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(1995)
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B., O.1
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4
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3843132551
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[2c] M. Egli, R. Polt, D. Seebach, Chimia 1989, 43, 4.
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(1989)
Chimia
, vol.43
, pp. 4
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Egli, M.1
Polt, R.2
Seebach, D.3
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6
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84986412991
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[3b] D. Seebach, J. D. Aebi, R. Naef, T. Weber, Helv. Chim. Acta 1985, 68, 144.
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(1985)
Helv. Chim. Acta
, vol.68
, pp. 144
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Seebach, D.1
Aebi, J.D.2
Naef, R.3
Weber, T.4
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7
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0003598098
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(Ed.: R. Scheffold), Springer Verlag, Berlin
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[3c] D. Seebach, R. Imwinkelried, T. Weber in Modern Synthetic Methods (Ed.: R. Scheffold), Springer Verlag, Berlin, 1986.
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(1986)
Modern Synthetic Methods
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Seebach, D.1
Imwinkelried, R.2
Weber, T.3
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8
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84987505887
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[3d] D. Seebach, E. Juaristi, D. D. Miller, C. Schickli, T. Weber, Helv. Chim. Acta 1987, 70, 237.
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(1987)
Helv. Chim. Acta
, vol.70
, pp. 237
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Seebach, D.1
Juaristi, E.2
Miller, D.D.3
Schickli, C.4
Weber, T.5
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10
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84986674631
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[3f] D. Seebach, E. Dziadulewicz, L. Behrendt, S. Cantoreggi, Liebigs Ann. Chem. 1989, 1215.
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(1989)
Liebigs Ann. Chem.
, pp. 1215
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Seebach, D.1
Dziadulewicz, E.2
Behrendt, L.3
Cantoreggi, S.4
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11
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0003598101
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(Eds.: B. Ernst, C. Leumann), Verlag Helvetica Chimica Acta (Basel) and VCH (Weinheim)
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D. Seebach, A. K. Beck, A. Studer in Modern Synthetic Methods (Eds.: B. Ernst, C. Leumann), Verlag Helvetica Chimica Acta (Basel) and VCH (Weinheim), 1995.
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(1995)
Modern Synthetic Methods
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Seebach, D.1
Beck, A.K.2
Studer, A.3
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17
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0027151899
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[7b] D. L. Boger, D. Yohannes, J. Zhou, M. A. Patane, J. Am. Chem. Soc. 1993, 115, 3420.
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(1993)
J. Am. Chem. Soc.
, vol.115
, pp. 3420
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Boger, D.L.1
Yohannes, D.2
Zhou, J.3
Patane, M.A.4
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18
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0028097524
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[7c] D. L. Boger, M. A. Patane, J. Zhou, J. Am. Chem. Soc. 1994, 116, 8544.
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(1994)
J. Am. Chem. Soc.
, vol.116
, pp. 8544
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Boger, D.L.1
Patane, M.A.2
Zhou, J.3
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21
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33748958868
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note
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We also synthesised the triglycine derivative with an imidazolidinone unit in the middle, see Scheme 1. However, this compound could be alkylated regioselectively only at its ester position, and we were unable to deprotect it by opening the imidazolidinone ring; consequently, we did not study it further.
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24
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33748963445
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note
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The electrophiles 10 and 16 were so reactive that they were slowly hydrolysed when in contact with silica gel under solvent-free conditions.
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25
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0000595888
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[13a] T. Maetzke, C. P. Hidber, D. Seebach, J. Am. Chem. Soc. 1990, 112, 8248.
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(1990)
J. Am. Chem. Soc.
, vol.112
, pp. 8248
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Maetzke, T.1
Hidber, C.P.2
Seebach, D.3
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27
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33748962208
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note
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We were not able to improve the reactivity by using three equiv. of LiHMDS as base or by trying to prepare the endo-cyclic monoenolate from the corresponding free acid 3 and two equiv. LDA.
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28
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33748986720
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note
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This problem became unsolvable with propionaldehyde, where reaction products could not be separated at all from the starting material.
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29
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33748980432
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note
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The reasons for these poor and not always reproducible yields are not clear. Especially in the case of alkylations via the dienolate there were substantial amounts of side products.
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30
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33748952135
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note
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[3e], the lower yields obtained here were rather unexpected. Since similar experiments with the corresponding Moc-protected imidazolidinone led to still lower yields (<15%), it seems to us that the aromatic ring of the Z-protecting group must play an important role in the alkylation of the enolates of these diglycine derivatives.
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31
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85086528260
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note
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4) nor by adding DMPU or LiBr.
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34
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0001199375
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[19b] W. A. König, I. Benecke, N. Lutch, E. Schmidt, J. Schulze, S. Sievers, J. Chromatogr. 1983, 279, 555.
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(1983)
J. Chromatogr.
, vol.279
, pp. 555
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König, W.A.1
Benecke, I.2
Lutch, N.3
Schmidt, E.4
Schulze, J.5
Sievers, S.6
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35
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33748973956
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note
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Attempts to alkylate the corresponding ester 4 at its endo-cyclic position led to a mixture of products alkylated in both endo-and exo-cyclic positions.
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36
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85086526874
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note
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[3].
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37
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85086526584
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note
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[5].
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39
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84987279356
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D. Seebach, T. L. Sommerfeld, Q. Jiang, L. M. Venanzi, Helv. Chim. Acta 1994, 77, 1313.
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(1994)
Helv. Chim. Acta
, vol.77
, pp. 1313
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Seebach, D.1
Sommerfeld, T.L.2
Jiang, Q.3
Venanzi, L.M.4
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40
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33748973791
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note
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This effect was also observed in experiments aimed towards deprotection of 21 and 27.
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46
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0000231464
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[27b] D. Seebach, O. Bezençon, B. Jaun, T. Pietzonka, J. L. Matthews, F. N. M. Kühnle, W. B. Schweizer, Helv. Chim. Acta 1996, 79, 588.
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(1996)
Helv. Chim. Acta
, vol.79
, pp. 588
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Seebach, D.1
Bezençon, O.2
Jaun, B.3
Pietzonka, T.4
Matthews, J.L.5
Kühnle, F.N.M.6
Schweizer, W.B.7
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47
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33748968502
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note
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The reaction of methyl iodide with 1 was slower than those of the bromides 10, 12, and 16.
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48
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0006938699
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Houston, Texas
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[29a] D. Seebach, Proceedings of The Robert A. Welch Foundation Conferences on Chemical Research, 1983, Houston, Texas, 1984, p. 93.
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(1984)
Proceedings of the Robert A. Welch Foundation Conferences on Chemical Research, 1983
, pp. 93
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Seebach, D.1
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49
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84987564680
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[29b] T. Laube, J. D. Dunitz, D. Seebach, Helv. Chim. Acta 1985, 68, 1373.
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(1985)
Helv. Chim. Acta
, vol.68
, pp. 1373
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Laube, T.1
Dunitz, J.D.2
Seebach, D.3
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53
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33748974633
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note
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It is well known that benzylic halides couple to 1,2-diphenyl-ethane derivatives upon treatment with alkyllithium.
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