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Recent reviews
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Recent reviews:
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0001485086
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(a) Li, A.-H.; Dai, L.-X.; Aggarwal, V. K. Chem. Rev. 1997, 97, 2341..
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(1997)
Chem. Rev.
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Li, A.-H.1
Dai, L.-X.2
Aggarwal, V.K.3
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9
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38349096680
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McGarrigle, E. M.; Myers, E. L.; Illa, O.; Shaw, M. A.; Riches, S. L.; Aggarwal, V. K. Chem. Rev. 2007, 107, 5841.
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Chem. Rev.
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McGarrigle, E.M.1
Myers, E.L.2
Illa, O.3
Shaw, M.A.4
Riches, S.L.5
Aggarwal, V.K.6
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10
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75749121940
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Selected representative examples
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Selected representative examples:
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11
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0001005657
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(a) Furukawa, N.; Sugihara, Y.; Fujihara, H. J. Org. Chem. 1989, 54, 4222.
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Furukawa, N.1
Sugihara, Y.2
Fujihara, H.3
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12
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0001283528
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(b) Aggarwal, V. K.; AbdelRahman, H.; Jones, R. V. H.; Standen, M. C. H. J. Am. Chem. Soc. 1994, 116, 5973.
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Aggarwal, V.K.1
Abdelrahman, H.2
Jones, R.V.H.3
Standen, M.C.H.4
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13
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0029900606
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(c)Aggarwal, V. K.; Ford, J. G.; Thompson, A.; Jones, R. V. H.; Standen, M. C. H. J. Am. Chem. Soc. 1996, 118, 7004.
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Aggarwal, V.K.1
Ford, J.G.2
Thompson, A.3
Jones, R.V.H.4
Standen, M.C.H.5
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14
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0035838866
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(d)Zanardi, J.; Leriverend, C.; Aubert, D.; Julienne, K.; Metzner, P. J. Org. Chem. 2001, 66, 5620.
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J. Org. Chem.
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Zanardi, J.1
Leriverend, C.2
Aubert, D.3
Julienne, K.4
Metzner, P.5
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15
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0035191959
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(e) Saito, T.; Akiba, D.; Sakairi, M.; Kanazawa, S. Tetrahedron Lett. 2001, 42, 57.
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Tetrahedron Lett.
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Saito, T.1
Akiba, D.2
Sakairi, M.3
Kanazawa, S.4
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16
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0037194180
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(f) Winn, C. L.; Bellenie, B. R.; Goodman, J. M. Tetrahedron Lett. 2002, 43, 5427.
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Tetrahedron Lett.
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Winn, C.L.1
Bellenie, B.R.2
Goodman, J.M.3
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17
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0041733341
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(g) Aggarwal, V. K.; Alonso, E.; Bae, I.; Hynd, G.; Lydon, K. M.; Palmer, M. J.; Patel, M.; Porcelloni, M.; Richardson, J.; Stenson, R. A.; Studley, J. R.; Vasse, J.-L; Winn, C. L J. Am. Chem. Soc. 2003, 125, 10926.
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(2003)
J. Am. Chem. Soc.
, vol.125
, pp. 10926
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Aggarwal, V.K.1
Alonso, E.2
Bae, I.3
Hynd, G.4
Lydon, K.M.5
Palmer, M.J.6
Patel, M.7
Porcelloni, M.8
Richardson, J.9
Stenson, R.A.10
Studley, J.R.11
Vasse, J.-L.12
Winn, C.L.13
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18
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18744373347
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(h) Davoust, M.; Brière, J.-F.; Jaffrès, P.A.; Metzner, P. J. Org. Chem. 2005, 70, 4166.
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J. Org. Chem.
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Davoust, M.1
Brière, J.-F.2
Jaffrès, P.A.3
Metzner, P.4
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19
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33746630913
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(i)Deng, X.-M.; Cai, P.; Ye, S.; Sun, X.-L.; Liao, W.-W.; Li, K.; Tang, Y.; Wu, Y.-D.; Dai, L.-X J. Am. Chem. Soc. 2006, 128, 9730.
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J. Am. Chem. Soc.
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Deng, X.-M.1
Cai, P.2
Ye, S.3
Sun, X.-L.4
Liao, W.-W.5
Li, K.6
Tang, Y.7
Wu, Y.-D.8
Dai, L.-X.9
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20
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43749091301
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(j) Davoust, M.; Cantagrel, F.; Metzner, P.; Brière, J.-F. Org. Biomol. Chem. 2008, 6, 1981.
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(2008)
Org. Biomol. Chem.
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Davoust, M.1
Cantagrel, F.2
Metzner, P.3
Brière, J.-F.4
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25
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0000677475
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(a) Aggarwal, V. K.; Ali, A.; Coogan, M. P. J. Org. Chem. 1997, 62, 8628.
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(1997)
J. Org. Chem.
, vol.62
, pp. 8628
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Aggarwal, V.K.1
Ali, A.2
Coogan, M.P.3
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26
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0036151392
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(b) Aggarwal, V. K.; Coogan, M. P.; Stenson, R. A.; Jones, R. V. H.; Fieldhouse, R.; Blacker, J. Eur. J. Org. Chem. 2002, 319.
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Eur. J. Org. Chem.
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Aggarwal, V.K.1
Coogan, M.P.2
Stenson, R.A.3
Jones, R.V.H.4
Fieldhouse, R.5
Blacker, J.6
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28
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75749103054
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Hiyama et al. (ref 7a) claimed that 2 could be synthesized in 97% ee in the presence of a chiral phase transfer catalyst. However our group (ref 7b) recently demonstrated that Hiyama was in error and has actually observed the decomposition of the catalyst to a related epoxide (with a relatively large specific rotation) during the formation of 2 as a racemate
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Hiyama et al. (ref 7a) claimed that 2 could be synthesized in 97% ee in the presence of a chiral phase transfer catalyst. However our group (ref 7b) recently demonstrated that Hiyama was in error and has actually observed the decomposition of the catalyst to a related epoxide (with a relatively large specific rotation) during the formation of 2 as a racemate:
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29
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0008772169
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(a) Hiyama, T.; Mishima, T.; Sawada, H.; Nozaki, H. J. Am. Chem. Soc. 1975, 97, 1626.
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(1975)
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Hiyama, T.1
Mishima, T.2
Sawada, H.3
Nozaki, H.4
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31
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note
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N2 ring closure to occur (see ref 9). It is notable however that in silico studies by Goodman (ref 10) on the enantioselective formation of styrene oxide from a semistabilized ylide derived from 4 and benzaldehyde found that the relative energies of the transition states of the intially formed betaines were excellent predictors of experimentally observed product enantioselectivity in the case studied. Thus, it cannot be ruled out that enantioselectivity can derive from kinetic control alone (i.e., facial selectivity in the attack of the ylide on the aldehyde) in these reactions, which would make the modest observed enantioselectivites associated with methylene transfer more difficult to explain.
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33
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0037157083
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(b) Aggarwal, V. K.; Harvey, J. N.; Richardson, J. J. Am. Chem. Soc. 2002, 124, 5747.
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(2002)
J. Am. Chem. Soc.
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Aggarwal, V.K.1
Harvey, J.N.2
Richardson, J.3
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34
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(c)Aggarwal, V. K.; Alonso, E.; Bae, I.; Hynd, G.; Lydon, K. M.; Palmer, M. J.; Patel, M.; Porcelloni, M.; Richardson, J.; Stenson, R. A.; Studley, J. R.; Vasse, J.-L.; Winn, C. L. J. Am. Chem. Soc. 2003, 125, 10926.
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(2003)
J. Am. Chem. Soc.
, vol.125
, pp. 10926
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Aggarwal, V.K.1
Alonso, E.2
Bae, I.3
Hynd, G.4
Lydon, K.M.5
Palmer, M.J.6
Patel, M.7
Porcelloni, M.8
Richardson, J.9
Stenson, R.A.10
Studley, J.R.11
Vasse, J.-L.12
Winn, C.L.13
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36
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33244460806
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(e) Aggarwal, V. K.; Charmant, J. P. H.; Fuentes, D.; Harvey, J. N.; Hynd, G.; Ohara, D.; Picoul, W.; Robiette, R.; Smith, C.; Vasse, J.-L.; Winn, C. L.; Am. Chem. Soc. 2006, 128, 2105.
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(2006)
Am. Chem. Soc.
, vol.128
, pp. 2105
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Aggarwal, V.K.1
Charmant, J.P.H.2
Fuentes, D.3
Harvey, J.N.4
Hynd, G.5
Ohara, D.6
Picoul, W.7
Robiette, R.8
Smith, C.9
Vasse, J.-L.10
Winn, C.L.11
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37
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38349138037
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(f) Edwards, D. R.; Montoya-Peleaz, P.; Crudden, C. M. Org. Lett. 2007, 9, 5481.
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(2007)
Org. Lett.
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Edwards, D.R.1
Montoya-Peleaz, P.2
Crudden, C.M.3
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38
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4043105034
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Silva, M. A.; Bellenie, B. R.; Goodman, J. M. Org. Lett. 2004, 6, 2559.
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(2004)
Org. Lett.
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Silva, M.A.1
Bellenie, B.R.2
Goodman, J.M.3
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39
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1H NMR spectroscopy did not indicate the formation of methanol
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1H NMR spectroscopy did not indicate the formation of methanol.
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40
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41549169617
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Kavanagh, S. A.; Piccinini, A.; Fleming, E. M.; Connon, S. J. Org. Biomol. Chem. 2008, 6, 1339.
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J. Org. Biomol. Chem.
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Kavanagh, S.A.1
Piccinini, A.2
Fleming, E.M.3
Connon, S.4
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41
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75749137413
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Phosphazene bases have been previously used in stoichiometric CC reactions involving semistabilsed ylides, for examples see
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Phosphazene bases have been previously used in stoichiometric CC reactions involving semistabilsed ylides, for examples see:
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42
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0034675294
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(a) SolladiéCavallo, A.; Bouérat, L.; Roje, M. Tetrahedron Lett. 2000, 41, 7309.
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(2000)
Tetrahedron Lett.
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Solladiécavallo, A.1
Bouérat, L.2
Roje, M.3
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43
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0042290869
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(b) Solladié-Cavallo, A.; Roje, M.; Isarno, T.; Sunjic, V.; Vinkovic, V. Eur. J. Org. Chem. 2000, 1077.
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Eur. J. Org. Chem.
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Solladié-Cavallo, A.1
Roje, M.2
Isarno, T.3
Sunjic, V.4
Vinkovic, V.5
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44
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0041853893
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Aggarwal, V. K.; Bae, I.; Lee, H.-Y.; Richardson, J.; Williams, D. T. Angew. Chem. Int. 2003, 42, 3274.
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(2003)
Angew. Chem. Int.
, vol.42
, pp. 3274
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Aggarwal, V.K.1
Bae, I.2
Lee, H.-Y.3
Richardson, J.4
Williams, D.T.5
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45
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0000920222
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Meinwald, J.; Labana, S. S.; Chadha, M. S. J. Am. Chem. Soc. 1963, 85, 582.
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Meinwald, J.1
Labana, S.S.2
Chadha, M.S.3
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46
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75749088985
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A key predictor of success in these experiments is having prior knowledge of the interval required to ensure complete alkylation of 9 (20 mol%) by MeOTf (20 mol%) at the concentration to be used in the epoxidation protocol.
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A key predictor of success in these experiments is having prior knowledge of the interval required to ensure complete alkylation of 9 (20 mol%) by MeOTf (20 mol%) at the concentration to be used in the epoxidation protocol.
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47
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75749129529
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Enantioselectivity in these reactions is strongly dependent on the steric bulk of the sulfide substituents; for instance, in an epoxidation experiment using a stoichiometric amount of the methyltriflate salt of a 2,5-dimethyl analogue of 27, (S)-2 was isolated in 1% ee.
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Enantioselectivity in these reactions is strongly dependent on the steric bulk of the sulfide substituents; for instance, in an epoxidation experiment using a stoichiometric amount of the methyltriflate salt of a 2,5-dimethyl analogue of 27, (S)-2 was isolated in 1% ee.
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