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0003544583
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(Ed.: I. Ojima), VCH, New York, Chap. 4.1
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R. A. Johnson, K. B. Sharpless in Catalytic Asymmetric Synthesis (Ed.: I. Ojima), VCH, New York, 1993, Chap. 4.1.
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Catalytic Asymmetric Synthesis
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Johnson, R.A.1
Sharpless, K.B.2
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0001269375
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K. B. Sharpless, Angew. Chem. 2002, 114, 2126-2135; Angew. Chem. Int. Ed. 2002, 41, 2024-2032. For important methodologies for the preparation of optically active aromatic epoxides, see T. Katsuki, Coord. Chem. Rev. 1995, 140, 189-214;
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Sharpless, K.B.1
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K. B. Sharpless, Angew. Chem. 2002, 114, 2126-2135; Angew. Chem. Int. Ed. 2002, 41, 2024-2032. For important methodologies for the preparation of optically active aromatic epoxides, see T. Katsuki, Coord. Chem. Rev. 1995, 140, 189-214;
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Angew. Chem. Int. Ed.
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0000775309
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K. B. Sharpless, Angew. Chem. 2002, 114, 2126-2135; Angew. Chem. Int. Ed. 2002, 41, 2024-2032. For important methodologies for the preparation of optically active aromatic epoxides, see T. Katsuki, Coord. Chem. Rev. 1995, 140, 189-214;
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Katsuki, T.1
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b) Y. Tu, Z.-X. Wang, Y. Shi, J. Am. Chem. Soc. 1996, 118, 9806-9807.
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Tu, Y.1
Wang, Z.-X.2
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0002178750
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J. M. Keith, J. F. Larrow, E. N. Jacobsen, Adv. Synth. Catal. 2001, 343, 5-26.
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Adv. Synth. Catal.
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Keith, J.M.1
Larrow, J.F.2
Jacobsen, E.N.3
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7
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0347659678
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a) M. Tokunaga, J. F. Larrow, F. Kakiuchi E. N. Jacobsen, Science 1997, 277, 937-938;
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Science
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Tokunaga, M.1
Larrow, J.F.2
Kakiuchi, F.3
Jacobsen, E.N.4
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8
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0029757771
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b) J. F. Larrow, S. E. Schaus, E. N. Jacobsen, J. Am. Chem. Soc. 1996, 118, 7420-7421;
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J. Am. Chem. Soc.
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Larrow, J.F.1
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0000656101
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e) R. Breinbauer, E. N. Jacobsen, Angew. Chem. 2000, 112, 3750-3753; Angew. Chem. Int. Ed. 2000, 39, 3604-3607;
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Breinbauer, R.1
Jacobsen, E.N.2
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0034675617
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e) R. Breinbauer, E. N. Jacobsen, Angew. Chem. 2000, 112, 3750-3753; Angew. Chem. Int. Ed. 2000, 39, 3604-3607;
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0346398727
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g) J. M. Ready, E. N. Jacobsen, Angew. Chem. 2002, 114, 1432-1435; Angew. Chem. Int. Ed. 2002, 41, 1374-1377.
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Ready, J.M.1
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g) J. M. Ready, E. N. Jacobsen, Angew. Chem. 2002, 114, 1432-1435; Angew. Chem. Int. Ed. 2002, 41, 1374-1377.
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15
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0033536712
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Kinetic resolution of 2,2-disubstituted epoxides catalyzed by [Cr(salen)]: H. Lebel, E. N. Jacobsen, Tetrahedron Lett. 1999, 40, 7303-7306.
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Lebel, H.1
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0003479152
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Springer, Berlin
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Kinetic resolution of 1,2-disubstituted epoxides with enzymes: K. Faber, Biotransformations in Organic Chemistry, Springer, Berlin, 2000, pp. 135-136.
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Faber, K.1
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0030605102
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Kinetic resolution of epoxides via C-heteroatom bond-forming reactions: a) S. E. Schaus, E. N. Jacobsen, Tetrahedron Lett. 1996, 37, 7937-7940;
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Tetrahedron Lett.
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Schaus, S.E.1
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0001501830
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b) S. E. Schaus, J. F. Larrow, E. N. Jacobsen, J. Org. Chem. 1997, 62, 4197-4199;
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Schaus, S.E.1
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Jacobsen, E.N.3
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0345664754
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c) L. E. Martinez, J. L. Leighton, D. H. Carsten, E. N. Jacobsen, J. Am. Chem. Soc. 1995, 117, 5897-5898;
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J. Am. Chem. Soc.
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Martinez, L.E.1
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f) J. Gu, M. J. Dirr, Y. Wang, D. L. Soper, B. De, J. A. Wos, C. R. Johnson, Org. Lett. 2001, 3, 791-794.
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Wos, J.A.6
Johnson, C.R.7
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23
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0001019669
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Important examples of ARO reactions of meso epoxides with carbon nucleophiles: a) M. B. Cole, K. D. Shimizu, C. A. Krueger, J. P. A. Harrity, M. L. Snapper, A. H. Hoveyda, Angew. Chem. 1996, 108, 1776-1779; Angew. Chem. Int. Ed. Engl. 1996, 35, 1668-1671;
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Cole, M.B.1
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Harrity, J.P.A.4
Snapper, M.L.5
Hoveyda, A.H.6
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24
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0029764025
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Important examples of ARO reactions of meso epoxides with carbon nucleophiles: a) M. B. Cole, K. D. Shimizu, C. A. Krueger, J. P. A. Harrity, M. L. Snapper, A. H. Hoveyda, Angew. Chem. 1996, 108, 1776-1779; Angew. Chem. Int. Ed. Engl. 1996, 35, 1668-1671;
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26
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0034104304
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c) M. Lautens, J.-L. Renaud, S. Hiebert, J. Am. Chem. Soc. 2000, 122, 1804-1805;
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0000299234
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d) M. Lautens, C. Dockendorff, K. Fagnou, A. Malicki, Org. Lett. 2002, 4, 1311-1314;
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Lautens, M.1
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0037239379
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e) M. Lautens, K. Fagnou, S. Hiebert, Acc. Chem. Res. 2003, 36, 48-58.
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0037178507
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M. Bandini, P. G. Cozzi, P. Melchiorre, A. Umani-Ronchi, J. Org. Chem. 2002, 67, 5386-5389.
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Bandini, M.1
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Umani-Ronchi, A.4
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32
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0347028845
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note
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Other indoles (indole; 1-methyl-, 5-methoxy-, 5-bromo-, 5-benzyloxy-, and 5-nitroindole) were less reactive than 2-methyindole.
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33
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0037138704
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Interestingly, the absolute configuration of isolated 1a was the opposite of that in other kinetic resolutions carried out with [Cr(salen)] and [Co(salen)] complexes, and this indicates that a different mechanism is probably operative in this case. For [Co(salen)]-catalyzed kinetic resolution, see S. E. Schaus, B. D. Brandes, J. F. Larrow, M. Tokunaga, K. B. Hansen, A. E. Gould, M. E. Furrow, E. N. Jacobsen, J. Am. Chem. Soc. 2002, 124, 1307-1315. For kinetic resolution employing [Cr(salen)], see ref. [7e].
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J. Am. Chem. Soc.
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Schaus, S.E.1
Brandes, B.D.2
Larrow, J.F.3
Tokunaga, M.4
Hansen, K.B.5
Gould, A.E.6
Furrow, M.E.7
Jacobsen, E.N.8
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34
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0000936493
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S. E. Schaus, J. Brånalt, E. N. Jacobsen, J. Org. Chem. 1998, 63, 403-405.
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J. Org. Chem.
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Schaus, S.E.1
Brånalt, J.2
Jacobsen, E.N.3
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35
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0346398726
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note
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Absolute configurations of products 2a, 2f, and 2i were established by HPLC analysis by comparing the retention times with those of authentic samples; for all other products the absolute configuration was assigned by analogy.
-
-
-
-
36
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0347659672
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note
-
The lower limit of the selectivity factor s for the epoxides was estimated by using the equation s=ln[1-c(1+ee)]/ ln[1-c(1-c(1-ee)] in the reaction with 2-methylindole (ee is the percentage enantiomeric excess of the ring-opened products; yields of ring-opened products were used for conversion c.
-
-
-
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37
-
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0346398721
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note
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The amount of 2-methylindole was adjusted to obtain the maximum yield possible with the highest enantiomeric excess for the unconverted epoxides. As we use 0.6-0.7 equiv of 2-methylindole, the maximum theoretical yield is 30-40%.
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-
-
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38
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0032532776
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Methylidene cyclohexene oxide could be resolved with a C-C bond-forming reaction: a) F. Baldassi, P. Crotti, F. Macchia, M. Pineschi, A. Arnold, B. L. Feringa, Tetrahedron Lett. 1998, 39, 7795-7798;
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Baldassi, F.1
Crotti, P.2
Macchia, F.3
Pineschi, M.4
Arnold, A.5
Feringa, B.L.6
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39
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0001423271
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b) F. Bertozzi, P. Crotti, F. Macchia, M. Pineschi, A. Arnold, B. L. Feringa, Org. Lett. 2000, 2, 933-936.
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Org. Lett.
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Bertozzi, F.1
Crotti, P.2
Macchia, F.3
Pineschi, M.4
Arnold, A.5
Feringa, B.L.6
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