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(a) Bailey, M.; Marko', I. E.; Ollis, W. D.; Rasmussen, P. R. Tetrahedron Lett. 1990, 31, 4509-4512.
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Bailey, M.1
Marko', I.E.2
Ollis, W.D.3
Rasmussen, P.R.4
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2
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Bailey, M.; Staton, I.; Ashton, P. R.; Marko', I. E.; Ollis, W. D. Tetrahedron: Asymmetry 1991, 2, 495- 509.
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Bailey, M.1
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Ashton, P.R.3
Marko', I.E.4
Ollis, W.D.5
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3
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0034640883
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To the best of our knowledge, these conditions were first reported in the following works: (a) Warrener, R. N.; Butler, D. N.; Margetic, D.; Pfeffer, F. M.; Russell, R. A. Tetrahedron Lett. 2000, 41, 4671-4675.
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To the best of our knowledge, these conditions were first reported in the following works: (a) Warrener, R. N.; Butler, D. N.; Margetic, D.; Pfeffer, F. M.; Russell, R. A. Tetrahedron Lett. 2000, 41, 4671-4675.
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4
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0037039032
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Pfeffer, F. M.; Russell, R. A. J. Chem. Soc., Perkin Trans. 1 2002, 2680- 2685. Although we have successfully used anhydrous solid potassium tertbutoxide in several experiments, for convenience we typically employ a 1.0 M stock solution of base in THF, prepared from the anhydrous solid (see the Supporting Information).
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Pfeffer, F. M.; Russell, R. A. J. Chem. Soc., Perkin Trans. 1 2002, 2680- 2685. Although we have successfully used anhydrous solid potassium tertbutoxide in several experiments, for convenience we typically employ a 1.0 M stock solution of base in THF, prepared from the anhydrous solid (see the Supporting Information).
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5
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0016386657
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Tanaka, S.; Yamamoto, H.; Nozaki, H.; Sharpless, K. B.; Michaelson, R. C.; Cutting, J. D. J. Am. Chem. Soc. 1974, 96, 5254-5255.
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Tanaka, S.1
Yamamoto, H.2
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Sharpless, K.B.4
Michaelson, R.C.5
Cutting, J.D.6
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6
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0030909214
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m-CPBA: Singleton, D. A.; Merrigan, S. R.; Liu, J.; Houk, K. N. J. Am. Chem. Soc. 1997, 119, 3385-3386, and references therein. Dimethyldioxirane: (a) Adam,W.; Curci, R.; Edwards, J. O. Acc. Chem. Res. 1989, 22, 205-211.
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m-CPBA: Singleton, D. A.; Merrigan, S. R.; Liu, J.; Houk, K. N. J. Am. Chem. Soc. 1997, 119, 3385-3386, and references therein. Dimethyldioxirane: (a) Adam,W.; Curci, R.; Edwards, J. O. Acc. Chem. Res. 1989, 22, 205-211.
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7
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66149165787
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and references therein
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Schneebeli, S. T.; Hall, M. L.; Breslow, R.; Friesner, R. J. Am. Chem. Soc. 2009, 131, 3965-3973, and references therein.
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J. Am. Chem. Soc
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Schneebeli, S.T.1
Hall, M.L.2
Breslow, R.3
Friesner, R.4
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10
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0041573564
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Wasserman, H. H.; Aubrey, N. E.; Zimmerman, H. E. J. Am. Chem. Soc. 1953, 75, 96-98.
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Wasserman, H.H.1
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Zimmerman, H.E.3
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0000814327
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and references therein
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(a) Zimmerman, H. E.; Singer, L.; Thyagarajan, B. S. J. Am. Chem. Soc. 1959, 81, 108-116, and references therein.
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Zimmerman, H.E.1
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6344260329
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Kelly, D. R.; Caroff, E.; Flood, R. W.; Heal, W.; Roberts, S. M. Chem. Commun. 2004, 2016- 2017.
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Chem. Commun
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Kelly, D.R.1
Caroff, E.2
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0000369178
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(a) Taniguchi, M.; Hino, T.; Kishi, Y. Tetrahedron Lett. 1986, 27, 4767-4770.
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Tetrahedron Lett
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Taniguchi, M.1
Hino, T.2
Kishi, Y.3
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5644224476
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Wei, H. X.; Hu, J.; Jasoni, R. L.; Li, G.; Pare', P. W. Helv. Chim. Acta 2004, 87, 2359-2363.
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Helv. Chim. Acta
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Wei, H.X.1
Hu, J.2
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Li, G.4
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18
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0038055666
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Rottländer, M.; Boymond, L.; Cahiez, G.; Knochel, P. J. Org. Chem. 1999, 64, 1080-1081.
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Rottländer, M.1
Boymond, L.2
Cahiez, G.3
Knochel, P.4
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19
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66149188167
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Metal-halogen exchange using i-PrMgCl and n-BuLi provided the following isolated yields of labeled substrates
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Metal-halogen exchange using i-PrMgCl and n-BuLi provided the following isolated yields of labeled substrates
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20
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66149185335
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: 13 (88% and 85%), 14 (77% and 52%), 15 (87% and 45%), and 16 (91% and 18%).
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: 13 (88% and 85%), 14 (77% and 52%), 15 (87% and 45%), and 16 (91% and 18%).
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21
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0001367039
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In the course of developing a synthetic route to the deuteriumlabeled substrates, we made the following observation: treatment of 3-deuteriopropiolate with diisobutylaluminum hydride-N-methylmorpholine- N-oxide complex (Ramachandran, P. V.; Reddy, M. V.; Rudd, M. T. Chem. Commun. 1999, 1979-1980) followed by addition of benzaldehyde afforded a 1:1 mixture of stereoisomeric (E)- and (Z)-alkenes. This stereochemical outcome is consistent with the intermediacy of an aluminum allenolate, as previously discussed by Tsuda et al. (Tsuda, T.; Yoshida, T.; Saegusa, T. J. Org. Chem. 1988, 53, 1037-1040).
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In the course of developing a synthetic route to the deuteriumlabeled substrates, we made the following observation: treatment of 3-deuteriopropiolate with diisobutylaluminum hydride-N-methylmorpholine- N-oxide complex (Ramachandran, P. V.; Reddy, M. V.; Rudd, M. T. Chem. Commun. 1999, 1979-1980) followed by addition of benzaldehyde afforded a 1:1 mixture of stereoisomeric (E)- and (Z)-alkenes. This stereochemical outcome is consistent with the intermediacy of an aluminum allenolate, as previously discussed by Tsuda et al. (Tsuda, T.; Yoshida, T.; Saegusa, T. J. Org. Chem. 1988, 53, 1037-1040).
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22
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37049075524
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Meth-Cohn et al. have reported examples of both stereospecific and non-stereospecific epoxidations with lithium tert-butylperoxide in THF ( (a) Clark, C.; Hermans, P.; Meth-Cohn, O.; Moore, C.; Taljaard, H. C.; van Vuuren, G. J. Chem. Soc., Chem. Commun. 1986, 1378-1380.
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Meth-Cohn et al. have reported examples of both stereospecific and non-stereospecific epoxidations with lithium tert-butylperoxide in THF ( (a) Clark, C.; Hermans, P.; Meth-Cohn, O.; Moore, C.; Taljaard, H. C.; van Vuuren, G. J. Chem. Soc., Chem. Commun. 1986, 1378-1380.
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23
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66149160282
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Meth- Cohn, O.; Moore, C.; Taljaard, H. C. J. Chem. Soc., Perkin Trans. 1, 1988 2663-2674.For example, these authors found that epoxidation of phenyl (Z)-2-phenylethenylsulfone proceeded with retention of stereochemistry, providing the corresponding cis epoxide in 90% yield, while epoxidation of di-tert-butyl maleate
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Meth- Cohn, O.; Moore, C.; Taljaard, H. C. J. Chem. Soc., Perkin Trans. 1, 1988 2663-2674).For example, these authors found that epoxidation of phenyl (Z)-2-phenylethenylsulfone proceeded with retention of stereochemistry, providing the corresponding cis epoxide in 90% yield, while epoxidation of di-tert-butyl maleate
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24
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66149185334
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proceeded with inversion of stereochemistry, providing the trans epoxide in 60% yield. We have examined the epoxidation of the latter substrate under the optimized conditions described above and found that the cis epoxide was formed with g95% stereospecificity in 80% yield after column chromatography see the Supporting Information
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proceeded with inversion of stereochemistry, providing the trans epoxide in 60% yield. We have examined the epoxidation of the latter substrate under the optimized conditions described above and found that the cis epoxide was formed with g95% stereospecificity in 80% yield after column chromatography (see the Supporting Information).
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26
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34547642886
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Christian, C. F.; Takeya, T; Szymanski, M. J.; Singleton, D. A. J. Org. Chem. 2007, 72, 6183-6189.
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J. Org. Chem
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Christian, C.F.1
Takeya, T.2
Szymanski, M.J.3
Singleton, D.A.4
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27
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33751552796
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For discussions of the diastereoselectivities of dihydroxylations of closely related substrates, see: a
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For discussions of the diastereoselectivities of dihydroxylations of closely related substrates, see: (a) Evans, D. A.; Kaldor, S. W. J. Org. Chem. 1990, 55, 1698-1700.
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(1990)
J. Org. Chem
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Evans, D.A.1
Kaldor, S.W.2
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0000386798
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Marko', I. E.; Giles, P. R.; Janousek, Z.; Hindley, N. J.; Declercq, J. P.; Tinant, B.; Feneau-Dupont, J.; Svendsen, J. S. Recl. Trav. Chim. Pays-Bas 1995, 114, 239-241.
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(1995)
Recl. Trav. Chim. Pays-Bas
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Marko', I.E.1
Giles, P.R.2
Janousek, Z.3
Hindley, N.J.4
Declercq, J.P.5
Tinant, B.6
Feneau-Dupont, J.7
Svendsen, J.S.8
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