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Perlmutter, P.1
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Reviews: (a) Schmalz, H. G. in Comprehensive Organic Synthesis; Trost, B. M., Fleming, I, Eds.; Pergamon: Oxford, 1991; Vol. 4, Chapter 1.5. (b) Rossiter, B. E.; Swingle, N. M. Chem. Rev. 1992, 92, 771. (c) Perlmutter, P. Conjugate Addition Reactions in Organic Synthesis; Pergamon Press: Oxford, 1992. For recent references see: (d) Urban, E.; Knühl, G.; Helmchen, G. Tetrahedron 1996, 52, 971. (e) Enders, D.; Kirchhoff, J.; Mannes, D.; Raabe, G. Synthesis 1995, 659.
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Knühl, G.2
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Reviews: (a) Schmalz, H. G. in Comprehensive Organic Synthesis; Trost, B. M., Fleming, I, Eds.; Pergamon: Oxford, 1991; Vol. 4, Chapter 1.5. (b) Rossiter, B. E.; Swingle, N. M. Chem. Rev. 1992, 92, 771. (c) Perlmutter, P. Conjugate Addition Reactions in Organic Synthesis; Pergamon Press: Oxford, 1992. For recent references see: (d) Urban, E.; Knühl, G.; Helmchen, G. Tetrahedron 1996, 52, 971. (e) Enders, D.; Kirchhoff, J.; Mannes, D.; Raabe, G. Synthesis 1995, 659.
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11944251609
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For an overview of our work see: (a) Carreño, M. C. Chem. Rev. 1995, 95, 1717. (b) Solladié, G.; Carreño, M. C. Organosulphur Chemistry: Synthetic Aspects; Page, P. C. B.,Ed.; Academic Press: New York, 1995; Chapter 1.
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11944251609
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Page, P. C. B.,Ed.; Academic Press: New York, Chapter 1
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For an overview of our work see: (a) Carreño, M. C. Chem. Rev. 1995, 95, 1717. (b) Solladié, G.; Carreño, M. C. Organosulphur Chemistry: Synthetic Aspects; Page, P. C. B.,Ed.; Academic Press: New York, 1995; Chapter 1.
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Organosulphur Chemistry: Synthetic Aspects
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Solladié, G.1
Carreño, M.C.2
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0001296747
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(a) Carreño, M. C.; García Ruano, J. L.; Martín, A. M.; Pedregal, C.; Rodríguez, J. H.; Rubio, A.; Sánchez, J.; Solladié, G. J. Org. Chem. 1990, 55, 2120.
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Martín, A.M.3
Pedregal, C.4
Rodríguez, J.H.5
Rubio, A.6
Sánchez, J.7
Solladié, G.8
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(b) Bueno, A. B.; Carreño, M. C.; García Ruano, J. L.; Peña, B.; Rubio, A.; Hoyos, M. A. Tetrahedron 1994, 50, 9355.
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Peña, B.4
Rubio, A.5
Hoyos, M.A.6
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14
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0027521372
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2AlCN also produced cyanhidrines diastereoselectively; see: Escribano, A. M.; García Ruano, J. L.; Martín-Castro, A. M.; Rodríguez, J. H. Tetrahedron 1994, 50, 7567.
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Maestro, M.C.3
Pérez González, M.4
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0029017569
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2AlCN also produced cyanhidrines diastereoselectively; see: Escribano, A. M.; García Ruano, J. L.; Martín-Castro, A. M.; Rodríguez, J. H. Tetrahedron 1994, 50, 7567.
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Tetrahedron Lett.
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Bueno, A.B.1
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García Ruano, J.L.3
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16
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0028282854
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2AlCN also produced cyanhidrines diastereoselectively; see: Escribano, A. M.; García Ruano, J. L.; Martín-Castro, A. M.; Rodríguez, J. H. Tetrahedron 1994, 50, 7567.
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Escribano, A.M.1
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Martín-Castro, A.M.3
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Carreño, M. C.; Pérez González, M.; Fischer, J. Tetrahedron Lett. 1995, 36, 4893.
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Carreño, M.C.1
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Fischer, J.3
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19
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3643094018
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note
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3 of the ethyl substituent (δ = 0.78 ppm) as a consequence of the anisotropic effect exerted by the spatially close aromatic ring. A similar effect could be observed in the proton or methyl group situated on the pro-R double bond of p-quinols 1 and 2.
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21
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0016716793
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(b) Collins, P. W.; Dajani, E. Z.; Bruhn, M. S.; Brown, C. H.; Palmer, J. R.; Pappo, R. Tetrahedron Lett. 1975, 4217. Hooz, J.; Layton, R. B. J. Am. Chem. Soc. 1971, 93, 7320.
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Collins, P.W.1
Dajani, E.Z.2
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Brown, C.H.4
Palmer, J.R.5
Pappo, R.6
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33947292075
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(b) Collins, P. W.; Dajani, E. Z.; Bruhn, M. S.; Brown, C. H.; Palmer, J. R.; Pappo, R. Tetrahedron Lett. 1975, 4217. Hooz, J.; Layton, R. B. J. Am. Chem. Soc. 1971, 93, 7320.
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Hooz, J.1
Layton, R.B.2
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23
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0028922199
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For recent references see: (a) Flemming, S.; Kabbara, J.; Nickisch, K.; Neh, H.; Westermann, J. Synthesis 1995, 317. (b) Kabbara, J.; Flemming, S.; Nickisch, K.; Neh, H.; Westermann, J. Tetrahedron 1995, 51, 743. (b) Westermann, J.; Nickisch, K. Angew. Chem., Int. Ed. Engl. 1993, 32, 1368.
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Synthesis
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Flemming, S.1
Kabbara, J.2
Nickisch, K.3
Neh, H.4
Westermann, J.5
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24
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0028893332
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For recent references see: (a) Flemming, S.; Kabbara, J.; Nickisch, K.; Neh, H.; Westermann, J. Synthesis 1995, 317. (b) Kabbara, J.; Flemming, S.; Nickisch, K.; Neh, H.; Westermann, J. Tetrahedron 1995, 51, 743. (b) Westermann, J.; Nickisch, K. Angew. Chem., Int. Ed. Engl. 1993, 32, 1368.
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Tetrahedron
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Kabbara, J.1
Flemming, S.2
Nickisch, K.3
Neh, H.4
Westermann, J.5
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25
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33748247204
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For recent references see: (a) Flemming, S.; Kabbara, J.; Nickisch, K.; Neh, H.; Westermann, J. Synthesis 1995, 317. (b) Kabbara, J.; Flemming, S.; Nickisch, K.; Neh, H.; Westermann, J. Tetrahedron 1995, 51, 743. (b) Westermann, J.; Nickisch, K. Angew. Chem., Int. Ed. Engl. 1993, 32, 1368.
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Angew. Chem., Int. Ed. Engl.
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(c) Rück, K.; Kunz, H. Angew. Chem., Int. Ed. Engl. 1991, 30, 694.
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0000749246
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(a) Solomon, M.; Jamison, W. C. L.; McCormick, M.; Liotta, D. C.; Cherry, D. A.; Mills, J. E.; Shah, R. D.; Rodgers, J. D.; Maryanoff, C. A. J. Am. Chem. Soc. 1988, 110, 3702.
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Shah, R.D.7
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0026574080
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(c) Swiss, K. A.; Hinkley, W.; Maryanoff, C. A.; Liotta, D. C. Synthesis 1992, 127.
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Swiss, K.A.1
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Fujioka, H.; Kitagaki, S.; Ohno, N.; Kitagawa, H.; Kita, Y.; Matsumoto, K. Tetrahedron: Asymmetry 1994, 5, 333.
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Fujioka, H.1
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Ohno, N.3
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Kita, Y.5
Matsumoto, K.6
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34
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3643136716
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note
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3. In this way, a 45:55 mixture of 4a and 4b was obtained. Thus, the result of the experience mentioned in the text suggests the mechanism proposed.
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