-
3
-
-
35948935339
-
-
The initial results on the yttrium-catalyzed opening of epoxycyclohexane and epoxycyclopentane are extracted from; Lin, M.-H. Yttrium-Catalyzed Reactions: Transacylation, Secondary Alcohol Resolution, Cyanosilylation of Ketones and Epoxides. Ph.D. Dissertation, The Ohio State University, 2002
-
The initial results on the yttrium-catalyzed opening of epoxycyclohexane and epoxycyclopentane are extracted from; Lin, M.-H. Yttrium-Catalyzed Reactions: Transacylation, Secondary Alcohol Resolution, Cyanosilylation of Ketones and Epoxides. Ph.D. Dissertation, The Ohio State University, 2002.
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-
-
-
4
-
-
0029764025
-
-
For leading references, see, for TMSCN: (a) Cole, B. M.; Shimizu, K. D.; Krueger, C. A.; Harrity, J. P. A.; Snapper, M. L.; Hoveyda, A. H. Angew. Chem., Int. Ed. Engl. 1996, 35, 1668.
-
For leading references, see, for TMSCN: (a) Cole, B. M.; Shimizu, K. D.; Krueger, C. A.; Harrity, J. P. A.; Snapper, M. L.; Hoveyda, A. H. Angew. Chem., Int. Ed. Engl. 1996, 35, 1668.
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-
-
-
6
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-
23844530814
-
-
Addition of TMSCN to aziridines: Mita, T.; Fujimori, I.; Wada, R.; Wen, J.; Kanai, M.; Shibasaki, M. J. Am. Chem. Soc. 2005, 127, 11252.
-
(c) Addition of TMSCN to aziridines: Mita, T.; Fujimori, I.; Wada, R.; Wen, J.; Kanai, M.; Shibasaki, M. J. Am. Chem. Soc. 2005, 127, 11252.
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-
-
-
7
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0001592395
-
-
For other notable results: (d) addition of an enolate
-
For other notable results: (d) addition of an enolate: Crotti, P.; Di Bussolo, V.; Favero, L.; Macchia, F.; Pineschi, M. Gazz. Chim Acta 1997, 127, 273.
-
(1997)
Gazz. Chim Acta
, vol.127
, pp. 273
-
-
Crotti, P.1
Di Bussolo, V.2
Favero, L.3
Macchia, F.4
Pineschi, M.5
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8
-
-
0032481031
-
-
Addition of PhLi: Oguni, N.; Miyagi, Y.; Itoh, K. Tetrahedron Lett. 1998, 39, 9023.
-
(e) Addition of PhLi: Oguni, N.; Miyagi, Y.; Itoh, K. Tetrahedron Lett. 1998, 39, 9023.
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-
-
-
9
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-
35948990909
-
-
Addition of alkynyllithium reagents: Zhu, C.; Yang, M.; Sun, J.; Zhu, Y.; Pan, Y. Synlett 2004, 465.
-
(f) Addition of alkynyllithium reagents: Zhu, C.; Yang, M.; Sun, J.; Zhu, Y.; Pan, Y. Synlett 2004, 465.
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-
-
-
10
-
-
0141605110
-
-
Addition of TMSCN with ephedrine Ga and In complexes gives isonitriles: Yuan, F.; Zhu, C.; Sun, J.; Liu, Y.; Pan, Y. J. Organomet. Chem. 2003, 682, 102.
-
(g) Addition of TMSCN with ephedrine Ga and In complexes gives isonitriles: Yuan, F.; Zhu, C.; Sun, J.; Liu, Y.; Pan, Y. J. Organomet. Chem. 2003, 682, 102.
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-
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11
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13944249839
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For a report of TMSCN-mediated ring opening of α,β-epoxy carboxamides catalyzed by Sm(III), see: Tosaki, S.; Tsuji, R.; Oshima, T.; Shibasaki, M. J. Am. Chem. Soc. 2005, 127, 2147.
-
(h) For a report of TMSCN-mediated ring opening of α,β-epoxy carboxamides catalyzed by Sm(III), see: Tosaki, S.; Tsuji, R.; Oshima, T.; Shibasaki, M. J. Am. Chem. Soc. 2005, 127, 2147.
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12
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0033920416
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For a review of asymmetric ring opening reactions of epoxides, see
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For a review of asymmetric ring opening reactions of epoxides, see: Jacobsen, E. Acc. Chem. Res. 2000, 33, 421.
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(2000)
Acc. Chem. Res
, vol.33
, pp. 421
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Jacobsen, E.1
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13
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8444233967
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For a compilation of more recent references, see
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For a compilation of more recent references, see: Schneider, C.; Sreekanth, A. R.; Mai, E. Angew. Chem., Int. Ed. 2004, 43, 5691.
-
(2004)
Angew. Chem., Int. Ed
, vol.43
, pp. 5691
-
-
Schneider, C.1
Sreekanth, A.R.2
Mai, E.3
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14
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0030766272
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Shimizu, K. D.; Cole, M. B.; Krueger, C. A.; Kuntz, K. W.; Snapper, M. L.; Hoveyda, A. H. Angew. Chem., Int. Ed. Engl. 1997, 36, 1704.
-
(1997)
Angew. Chem., Int. Ed. Engl
, vol.36
, pp. 1704
-
-
Shimizu, K.D.1
Cole, M.B.2
Krueger, C.A.3
Kuntz, K.W.4
Snapper, M.L.5
Hoveyda, A.H.6
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15
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0033920416
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3 to epoxycyclohexane. (a) See: Jacobsen, E. Acc. Chem. Res. 2000, 33, 421 and references cited therein.
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3 to epoxycyclohexane. (a) See: Jacobsen, E. Acc. Chem. Res. 2000, 33, 421 and references cited therein.
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16
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0032556244
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10780. Footnote 7 of this paper is especially relevant to the present discussion
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(b) Konsler, R. G.; Karl, J.; Jacobsen, E. N. J. Am. Chem. Soc. 1998, 120, 10780. Footnote 7 of this paper is especially relevant to the present discussion.
-
(1998)
J. Am. Chem. Soc
, vol.120
-
-
Konsler, R.G.1
Karl, J.2
Jacobsen, E.N.3
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17
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0025131291
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Anecdotal evidence for such inhibition by chloride ion can be found in the early experiments of Utimoto who showed that lanthanide chlorides are poor catalysts for the reaction between epoxycyclohexane and TMSCN. See: Matsubara, S, Onishi, H, Utimoto, K. Tetrahedron Lett. 1990, 31, 6209
-
Anecdotal evidence for such inhibition by chloride ion can be found in the early experiments of Utimoto who showed that lanthanide chlorides are poor catalysts for the reaction between epoxycyclohexane and TMSCN. See: Matsubara, S.; Onishi, H.; Utimoto, K. Tetrahedron Lett. 1990, 31, 6209.
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18
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4744366734
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For a discussion of low coordinate Y-complexes, see
-
For a discussion of low coordinate Y-complexes, see: Schuetz, S. A.; Silvernail, C. M.; Incarvito, C. D.; Rheingold, A. L.; Clark, J. L.; Day, V. W.; Belot, J. A. Inorg. Chem. 2004, 23, 6203.
-
(2004)
Inorg. Chem
, vol.23
, pp. 6203
-
-
Schuetz, S.A.1
Silvernail, C.M.2
Incarvito, C.D.3
Rheingold, A.L.4
Clark, J.L.5
Day, V.W.6
Belot, J.A.7
-
19
-
-
0002813774
-
-
Runte, O.; Priermeier, T.; Anwander, R. J. Chem. Soc., Chem. Commun. 1996, 1385.
-
(1996)
J. Chem. Soc., Chem. Commun
, pp. 1385
-
-
Runte, O.1
Priermeier, T.2
Anwander, R.3
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20
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35949003664
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-
For full experimental details, including the preparation and use of the ligands listed in Figure 1, see the Supporting Information. Details of the spectroscopic and chromatographic identification of compounds are also included there.
-
For full experimental details, including the preparation and use of the ligands listed in Figure 1, see the Supporting Information. Details of the spectroscopic and chromatographic identification of compounds are also included there.
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21
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33749115448
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For the synthesis of the amides, see
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For the synthesis of the amides, see: Anwander, R.; Runte, O.; Eppinger, J.; Gerstberger, G.; Herdtweck, E.; Spiegler, M. J. Chem. Soc., Dalton Trans. 1998, 847.
-
(1998)
J. Chem. Soc., Dalton Trans
, pp. 847
-
-
Anwander, R.1
Runte, O.2
Eppinger, J.3
Gerstberger, G.4
Herdtweck, E.5
Spiegler, M.6
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22
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35948933552
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Jacobsen has reported that 1 mol, of a monomeric (salen)Cr-N3 complex is needed effect the opening of epoxycyclopentane with TMS-N 3 under these conditions see ref 6
-
3 under these conditions (see ref 6).
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23
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35948966885
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Crystallographic details for 6 and a figure representing thermal ellipsoids are included in the Supporting Information.
-
Crystallographic details for 6 and a figure representing thermal ellipsoids are included in the Supporting Information.
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-
24
-
-
0035793293
-
-
2: Mascarenhas, C. M.; Miller, S. P.; White, P. S.; Morken, J. P. Angew. Chem., Int. Ed. 2001, 40, 601.
-
2: Mascarenhas, C. M.; Miller, S. P.; White, P. S.; Morken, J. P. Angew. Chem., Int. Ed. 2001, 40, 601.
-
-
-
-
25
-
-
0002813774
-
-
(b) Runte, O.; Priermeier, T.; Anwander, R. J. Chem. Soc., Chem. Commun. 1996, 1385.
-
(1996)
J. Chem. Soc., Chem. Commun
, pp. 1385
-
-
Runte, O.1
Priermeier, T.2
Anwander, R.3
-
26
-
-
84944508767
-
-
(c) Herrmann, W. A.; Anwander, R.; Munck, F. C.; Scherer, W.; Dufaud, V.; Huber, N. W.; Artus, G. R. J. Z. Naturforsch., B 1994, 49, 1789.
-
(1994)
Z. Naturforsch., B
, vol.49
, pp. 1789
-
-
Herrmann, W.A.1
Anwander, R.2
Munck, F.C.3
Scherer, W.4
Dufaud, V.5
Huber, N.W.6
Artus, G.R.J.7
-
27
-
-
0033590687
-
-
(d) Evans, W. J.; Fujimoto, C. H.; Ziller, J. W. J. Chem. Soc., Chem. Commun. 1999, 311.
-
(1999)
J. Chem. Soc., Chem. Commun
, pp. 311
-
-
Evans, W.J.1
Fujimoto, C.H.2
Ziller, J.W.3
-
28
-
-
0037138628
-
-
An alkoxide bridged dimer: Ovitt, T. M, Coates, G. W. J. Am. Chem. Soc. 2002, 124, 1316. Al
-
(e) An alkoxide bridged dimer: Ovitt, T. M.; Coates, G. W. J. Am. Chem. Soc. 2002, 124, 1316. Al:
-
-
-
-
29
-
-
0035907043
-
-
Al(L4)X: Evans, D. A.; Janey, J. M.; Magomedov, N.; Tedrow, J. S. Angew. Chem., Int. Ed. 2001, 40, 1884.
-
(f) Al(L4)X: Evans, D. A.; Janey, J. M.; Magomedov, N.; Tedrow, J. S. Angew. Chem., Int. Ed. 2001, 40, 1884.
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-
-
-
30
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0001515027
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-
In the ring-opening reaction of epoxycyclohexane by TMSCN, selective formation of a nitrile or an isonitrile product can be achieved by the choice of Lewis acids. Thus, Zn, Pd, Sn, In, and Ga salts give the isonitrile, whereas Ca, Mg, Zn, Y, Ti, and most lanthanide salts give the nitrile. Isonitrile: (a) Gassman, P. G, Guggenheim, T. L. J. Am. Chem. Soc. 1982, 104, 5849
-
In the ring-opening reaction of epoxycyclohexane by TMSCN, selective formation of a nitrile or an isonitrile product can be achieved by the choice of Lewis acids. Thus, Zn, Pd, Sn, In, and Ga salts give the isonitrile, whereas Ca, Mg, Zn, Y, Ti, and most lanthanide salts give the nitrile. Isonitrile: (a) Gassman, P. G.; Guggenheim, T. L. J. Am. Chem. Soc. 1982, 104, 5849.
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-
-
-
31
-
-
0007412648
-
-
(b) Spessard, G. O.; Ritter, A. R.; Johnson, D. M.; Montgomery, A. M. Tetrahedron Lett. 1983, 24, 655.
-
(1983)
Tetrahedron Lett
, vol.24
, pp. 655
-
-
Spessard, G.O.1
Ritter, A.R.2
Johnson, D.M.3
Montgomery, A.M.4
-
32
-
-
0000995996
-
-
(c) Imi, K.; Yanagihara, N.; Utimoto, K. J. Org. Chem. 1987, 52, 1013.
-
(1987)
J. Org. Chem
, vol.52
, pp. 1013
-
-
Imi, K.1
Yanagihara, N.2
Utimoto, K.3
-
33
-
-
0037459471
-
-
(d) Zhu, C.; Yuan, F.; Gu, W.; Pan, Y. Chem. Commun. 2003, 692.
-
(2003)
Chem. Commun
, pp. 692
-
-
Zhu, C.1
Yuan, F.2
Gu, W.3
Pan, Y.4
-
37
-
-
0000063651
-
-
(h) Sugita, K.; Ohta, A.; Onaka, M.; Izumi, Y. Chem. Lett. 1990, 481.
-
(1990)
Chem. Lett
, pp. 481
-
-
Sugita, K.1
Ohta, A.2
Onaka, M.3
Izumi, Y.4
-
38
-
-
0025131291
-
-
Matsubara, S.; Onishi, H.; Utimoto, K. Tetrahedron Lett. 1990, 31, 6209. See also refs 3a,b,g.
-
(i) Matsubara, S.; Onishi, H.; Utimoto, K. Tetrahedron Lett. 1990, 31, 6209. See also refs 3a,b,g.
-
-
-
-
39
-
-
1842528335
-
-
For IR spectroscopy of bridged nitrile/isonitrile complexes, see: (a) Sheng, T.; H. Vahrenkamp, H. Inorg. Chim. Acta 2004, 357, 1739.
-
For IR spectroscopy of bridged nitrile/isonitrile complexes, see: (a) Sheng, T.; H. Vahrenkamp, H. Inorg. Chim. Acta 2004, 357, 1739.
-
-
-
-
40
-
-
0011669369
-
-
(b) Dixon, D. A.; Hertler, W. R.; Chase, D. B.; Farnham, W. B.; Davidson, F. Inorg. Chem. 1988, 27, 4012.
-
(1988)
Inorg. Chem
, vol.27
, pp. 4012
-
-
Dixon, D.A.1
Hertler, W.R.2
Chase, D.B.3
Farnham, W.B.4
Davidson, F.5
-
41
-
-
0037493110
-
-
Plecnik, C. E.; Liu, S.; Shore, S. S. Acc. Chem. Res. 2003, 36, 499.
-
(2003)
Acc. Chem. Res
, vol.36
, pp. 499
-
-
Plecnik, C.E.1
Liu, S.2
Shore, S.S.3
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