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1
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0033690703
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For reviews on utility of stereoselective vinylogous Mannich reactions, see: a) G. Casiraghi, F. Zanardi, G. Appendino, G. Rassu, Chem. Rev. 2000, 100, 1929-1972;
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Casiraghi, G.1
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Rassu, G.4
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3
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0027130840
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For example, see
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For example, see: a) S. F. Martin, S. Liras, J. Am. Chem. Soc. 1993, 115, 10450-10451;
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Martin, S.F.1
Liras, S.2
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4
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0034820002
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b) S. Liras, C. L. Lynch, A. M. Fryer, B. T. Vu, S. F. Martin, J. Am. Chem. Soc. 2001, 123, 5918-5924;
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J. Am. Chem. Soc.
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Liras, S.1
Lynch, C.L.2
Fryer, A.M.3
Vu, B.T.4
Martin, S.F.5
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5
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2942592472
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c) M. V. Spanedda, M. Ourévitch, B. Crousse, J.-P. Bègué, D. Bonnet-Delopn, Tetrahedron Lett. 2004, 45, 5023-5025.
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Spanedda, M.V.1
Ourévitch, M.2
Crousse, B.3
Bègué, J.-P.4
Bonnet-Delopn, D.5
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6
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1642415515
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For a review of Mannich reactions, see
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For a review of Mannich reactions, see: a) A. Córdova, Acc. Chem. Res. 2004, 37, 102-112;
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Acc. Chem. Res.
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Córdova, A.1
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7
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3042550754
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for select recent reports of catalytic asymmetric Mannich reactions (not AVM), see: b) T. Hamada, K. Manabe, S. Kobayashi, J. Am. Chem. Soc. 2004, 126, 7768-7769;
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(2004)
J. Am. Chem. Soc.
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Hamada, T.1
Manabe, K.2
Kobayashi, S.3
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8
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3242668608
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c) S. Matsunaga, T. Yoshida, H. Morimoto, N. Kumagai, M. Shibasaki, J. Am. Chem. Soc. 2004, 126, 8777-8785;
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J. Am. Chem. Soc.
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Matsunaga, S.1
Yoshida, T.2
Morimoto, H.3
Kumagai, N.4
Shibasaki, M.5
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9
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21244500409
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d) Y. Hamashima, N. Sasamoto, D. Hotta, H. Somei, N. Umebayashi, M. Sodeoka, Angew. Chem. 2005, 117, 1549-1553;
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Angew. Chem.
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Hamashima, Y.1
Sasamoto, N.2
Hotta, D.3
Somei, H.4
Umebayashi, N.5
Sodeoka, M.6
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10
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16244364063
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Angew. Chem. Int. Ed. 2005, 44, 1525-1529;
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(2005)
Angew. Chem. Int. Ed.
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12
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20644448209
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Angew. Chem. Int. Ed. 2005, 44, 3600-3603;
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(2005)
Angew. Chem. Int. Ed.
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13
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33646511310
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f) J. Song, Y. Wang, L. Deng, J. Am. Chem. Soc. 2006, 128, 6048-6049;
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J. Am. Chem. Soc.
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Song, J.1
Wang, Y.2
Deng, L.3
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16
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4644355914
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D. Uraguchi, K. Sorimachi, M. Terada, J. Am. Chem. Soc. 2004, 126, 11804-11805.
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J. Am. Chem. Soc.
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Uraguchi, D.1
Sorimachi, K.2
Terada, M.3
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17
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0001209391
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For related Ag-catalyzed Mannich-type reactions (not AVM), see: a) D. Ferraris, B. Young, T. Dudding, T. Lectka, J. Am. Chem. Soc. 1998, 120, 4548-4549;
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(1998)
J. Am. Chem. Soc.
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Ferraris, D.1
Young, B.2
Dudding, T.3
Lectka, T.4
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18
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0037427326
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b) N. S. Josephsohn, M. L. Snapper, A. H. Hoveyda, J. Am. Chem. Soc. 2003, 125, 4018-4019;
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J. Am. Chem. Soc.
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Josephsohn, N.S.1
Snapper, M.L.2
Hoveyda, A.H.3
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19
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1642398587
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c) N. S. Josephsohn, M. L. Snapper, A. H. Hoveyda, J. Am. Chem. Soc. 2004, 126, 3734-3735;
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J. Am. Chem. Soc.
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Josephsohn, N.S.1
Snapper, M.L.2
Hoveyda, A.H.3
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20
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28244483115
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d) N. S. Josephsohn, E. L. Carswell, M. L. Snapper, A. H. Hoveyda, Org. Lett. 2005, 7, 2711-2713.
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Org. Lett.
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Josephsohn, N.S.1
Carswell, E.L.2
Snapper, M.L.3
Hoveyda, A.H.4
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21
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33750974392
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note
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For determination of relative and absolute stereochemical identity of AVM products from reactions of 3, see the Supporting Information.
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22
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33750972816
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note
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See the Supporting Information for all data.
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23
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0037241494
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For relative p nucleophilicity of various enol silanes, see: H. Mayr, B. Kempf, A. R. Ofial, Acc. Chem. Res. 2003, 36, 66-77.
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Acc. Chem. Res.
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Mayr, H.1
Kempf, B.2
Ofial, A.R.3
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24
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0346162171
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For a similar effect in Cr-catalyzed enantioselective aldol additions of siloxyfurans to aldehydes, see: S. Onitsuka, Y. Matsuoka, R. Irie, T. Katsuki, Chem. Lett. 2003, 32, 974-975.
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Chem. Lett.
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Onitsuka, S.1
Matsuoka, Y.2
Irie, R.3
Katsuki, T.4
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25
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33751019603
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note
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2O (conditions in Table 1).
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26
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33750988150
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note
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Relative and absolute stereochemical identity of products derived from 5 was established through an X-ray crystal structure of 6j (entry 5, Table 2). See the Supporting Information for details.
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27
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33751006380
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note
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For relative and absolute stereochemical identity of products derived from 7, see the Supporting Information.
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28
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33750981464
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note
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3N (synthesis of 4a with 1 mol% 1a, -78°C).
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29
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0034597491
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Preference for endo-type ("Diels-Alder"-type) transition states has been suggested for diastereoselective (non-asymmetric) vinylogous Mannich reactions; see: S. K. Burr, S. F. Martin, Org. Lett. 2000, 2, 3445-3447.
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(2000)
Org. Lett.
, vol.2
, pp. 3445-3447
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Burr, S.K.1
Martin, S.F.2
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30
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33750993981
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note
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The C=N bond of chiral ligands do not undergo addition likely because of steric hinderance provided by the amino acid substituent.
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31
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15744387149
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and references therein
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Pre-association of the amide moiety with the siloxyfuran is also feasible; such an interaction would enhance enolsilane nucleophilicity and facilitate delivery; see: a) S. E. Denmark, G. L. Beutner, T. Wynn, M. D. Eastgate, J. Am. Chem. Soc. 2005, 127, 3774-3789, and references therein;
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J. Am. Chem. Soc.
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Denmark, S.E.1
Beutner, G.L.2
Wynn, T.3
Eastgate, M.D.4
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32
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33748413162
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b) Y. Zhao, J. Rodrigo, A. H. Hoveyda, M. L. Snapper, Nature 2006, 443, 67-70.
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(2006)
Nature
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Zhao, Y.1
Rodrigo, J.2
Hoveyda, A.H.3
Snapper, M.L.4
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33
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0035944511
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a) J. R. Porter, J. F. Traverse, A. H. Hoveyda, M. L. Snapper, J. Am. Chem. Soc. 2001, 123, 10409-10410;
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J. Am. Chem. Soc.
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Porter, J.R.1
Traverse, J.F.2
Hoveyda, A.H.3
Snapper, M.L.4
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17144414055
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b) L. C. Akullian, M. L. Snapper, A. H. Hoveyda, Angew. Chem. 2003, 115, 4376-4379;
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(2003)
Angew. Chem.
, vol.115
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Akullian, L.C.1
Snapper, M.L.2
Hoveyda, A.H.3
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35
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0141633628
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Angew. Chem. Int. Ed. 2003, 42, 4244-4247.
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(2003)
Angew. Chem. Int. Ed.
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, pp. 4244-4247
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36
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33750972243
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note
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Preliminary results show that the present procedure is applicable to AVM of aldimines derived from aliphatic aldehydes.
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