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0242681793
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note
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Examples of stereochemical reversal in the reduction of cyclopropyl ketones when an electrophilic reducing agent DIBAL-H was used: see ref 8d,e,f.
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-
46
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0000163873
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Stereocontrol in carbon - nucleophile additions to trans-cyclopropyl carbonyls is also known to be exceedingly difficult, see: Critcher, D. J.; Connolly, S.; Wills, M. J. Org. Chem. 1997, 62, 6638-6657.
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2142858450
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The stereochemistries of the reduction products were determined by the modified Mosher's method (Ohtani, I.; Kusumi, T.; Kashman, Y.; Kakisawa, H. J. Am. Chem. Soc, 1991, 113, 4092-4096); see the Supporting Information.
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0242681792
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note
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3 did not suggest a stable conformation in solution, and crystals of the transsubstituted ketones 1a-e and 2 suitable for X-ray crystallographic analysis were not obtained.
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49
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0004133516
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Gaussian, Inc., Pittsburgh, PA
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Gaussian 98, Revision A.6: Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Zakrzewski, V. G.; Montgomery, Jr., J. A.; Stratmann, R. E.; Burant, J. C.; Dapprich, S.; Millam, J. M.; Daniels, A. D.; Kudin, K. N.; Strain, M. C.; Farkas, O.; Tomasi, J.; Barone, V.; Cossi, M.; Cammi, R.; Mennucci, B.; Pomelli, C.; Adamo, C.; Clifford, S.; Ochterski, J.; Petersson, G. A.; Ayala, P. Y.; Cui, Q.; Morokuma, K.; Malick, D. K.; Rabuck, A. D.; Raghavachari, K.; Foresman, J. B.; Cioslowski, J.; Ortiz, J. V.; Stefanov, B. B.; Liu, G.; Liashenko, A.; Piskorz, P.; Komaromi, I.; Gomperts, R.; Martin, R. L.; Fox, D. J.; Keith, T.; Al-Laham, M. A.; Peng, C. Y.; Nanayakkara, A.; Gonzalez, C.; Challacombe, M.; Gill, P. M. W.; Johnson, B.; Chen, W.; Wong, M. W.; Andres, J. L.; Gonzalez, C.; Head-Gordon, M.; Replogle, E. S.; Pople, J. A. Gaussian, Inc., Pittsburgh, PA, 1998.
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Gaussian 98, Revision A.6
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Frisch, M.J.1
Trucks, G.W.2
Schlegel, H.B.3
Scuseria, G.E.4
Robb, M.A.5
Cheeseman, J.R.6
Zakrzewski, V.G.7
Montgomery J.A., Jr.8
Stratmann, R.E.9
Burant, J.C.10
Dapprich, S.11
Millam, J.M.12
Daniels, A.D.13
Kudin, K.N.14
Strain, M.C.15
Farkas, O.16
Tomasi, J.17
Barone, V.18
Cossi, M.19
Cammi, R.20
Mennucci, B.21
Pomelli, C.22
Adamo, C.23
Clifford, S.24
Ochterski, J.25
Petersson, G.A.26
Ayala, P.Y.27
Cui, Q.28
Morokuma, K.29
Malick, D.K.30
Rabuck, A.D.31
Raghavachari, K.32
Foresman, J.B.33
Cioslowski, J.34
Ortiz, J.V.35
Stefanov, B.B.36
Liu, G.37
Liashenko, A.38
Piskorz, P.39
Komaromi, I.40
Gomperts, R.41
Martin, R.L.42
Fox, D.J.43
Keith, T.44
Al-Laham, M.A.45
Peng, C.Y.46
Nanayakkara, A.47
Gonzalez, C.48
Challacombe, M.49
Gill, P.M.W.50
Johnson, B.51
Chen, W.52
Wong, M.W.53
Andres, J.L.54
Gonzalez, C.55
Head-Gordon, M.56
Replogle, E.S.57
Pople, J.A.58
more..
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50
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0001181977
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The conformation of the transition state and the intermediate can be strongly influenced by conformational effects which stabilize the ground state conformation, for examples see: (a) Pothier, N.; Goldstein, S.; Deslongchamps, P. Helv. Chim Acta 1992, 75, 604-620.
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Helv. Chim Acta
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Pothier, N.1
Goldstein, S.2
Deslongchamps, P.3
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(b) Romero, J. A. C.; Tabacco, S. A.; Woerpel, K. A. J. Am. Chem. Soc. 2000, 122, 168-189.
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J. Am. Chem. Soc.
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Romero, J.A.C.1
Tabacco, S.A.2
Woerpel, K.A.3
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(c) Abe, H.; Shuto, S.; Matsuda, A. J. Am. Chem. Soc. 2001, 123, 11870-11882.
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J. Am. Chem. Soc.
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Abe, H.1
Shuto, S.2
Matsuda, A.3
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(d) Tamura, A.; Abe, H.; Matsuda, A. Shuto, S. Angew. Chem., Int. Ed. 2003, 42, 1021-1023.
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Angew. Chem., Int. Ed.
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Tamura, A.1
Abe, H.2
Matsuda, A.3
Shuto, S.4
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