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For the most recent work in this area, see the following and references cited therein (a) Bonini, C.; Racioppi, R.; Righi, G.; Rossi, L. Tetrahedron. Asymmetry 1994, 5, 173-176. (b) Kaneko, Y.; Matsuo, T.; Kiyooka, S. Tetrahedron Lett. 1994, 35, 4107-4110. (c) Mohr, P. Tetrahedron Lett. 1991, 32, 2219-2222. (d) Bonini, C.; Bianco, A.; Di Fabio, R.; Mecozzi, S.; Proposito, A., Righi, G. Gazz. Chim. Ital. 1991, 121, 75-80. (e) Evans, D. A.; Hoveyda, A. H. J Org. Chem. 1990, 55, 5190-5192. (f) Evans, D. A.; Hoveyda, A. H. J. Am. Chem. Soc. 1990, 112, 6447-6449.
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For the most recent work in this area, see the following and references cited therein (a) Bonini, C.; Racioppi, R.; Righi, G.; Rossi, L. Tetrahedron. Asymmetry 1994, 5, 173-176. (b) Kaneko, Y.; Matsuo, T.; Kiyooka, S. Tetrahedron Lett. 1994, 35, 4107-4110. (c) Mohr, P. Tetrahedron Lett. 1991, 32, 2219-2222. (d) Bonini, C.; Bianco, A.; Di Fabio, R.; Mecozzi, S.; Proposito, A., Righi, G. Gazz. Chim. Ital. 1991, 121, 75-80. (e) Evans, D. A.; Hoveyda, A. H. J Org. Chem. 1990, 55, 5190-5192. (f) Evans, D. A.; Hoveyda, A. H. J. Am. Chem. Soc. 1990, 112, 6447-6449.
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For the most recent work in this area, see the following and references cited therein (a) Bonini, C.; Racioppi, R.; Righi, G.; Rossi, L. Tetrahedron. Asymmetry 1994, 5, 173-176. (b) Kaneko, Y.; Matsuo, T.; Kiyooka, S. Tetrahedron Lett. 1994, 35, 4107-4110. (c) Mohr, P. Tetrahedron Lett. 1991, 32, 2219-2222. (d) Bonini, C.; Bianco, A.; Di Fabio, R.; Mecozzi, S.; Proposito, A., Righi, G. Gazz. Chim. Ital. 1991, 121, 75-80. (e) Evans, D. A.; Hoveyda, A. H. J Org. Chem. 1990, 55, 5190-5192. (f) Evans, D. A.; Hoveyda, A. H. J. Am. Chem. Soc. 1990, 112, 6447-6449.
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For the most recent work in this area, see the following and references cited therein (a) Bonini, C.; Racioppi, R.; Righi, G.; Rossi, L. Tetrahedron. Asymmetry 1994, 5, 173-176. (b) Kaneko, Y.; Matsuo, T.; Kiyooka, S. Tetrahedron Lett. 1994, 35, 4107-4110. (c) Mohr, P. Tetrahedron Lett. 1991, 32, 2219-2222. (d) Bonini, C.; Bianco, A.; Di Fabio, R.; Mecozzi, S.; Proposito, A., Righi, G. Gazz. Chim. Ital. 1991, 121, 75-80. (e) Evans, D. A.; Hoveyda, A. H. J Org. Chem. 1990, 55, 5190-5192. (f) Evans, D. A.; Hoveyda, A. H. J. Am. Chem. Soc. 1990, 112, 6447-6449.
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2 were substituted successfully for reducing agents with the syn-to-anti ratio exceeding 98:2 and 74-87% yields.
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85088622062
-
-
note
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3 led to 69:31 (84%) and 60:40 (81%) syn-to-anti ratios, respectively.
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33748542524
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85088621119
-
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note
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3, 87:13.
-
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31
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5344248133
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-
note
-
Derived from molecular mechanics (PCMODEL Version 4.51: Serena Software, Bloomington, IN 47402), strain energies (kcal/mol for the following isomers of 1-chloro-3-methylcyclohexane: cis, all equatorial -7.19, all axial -10.63; trans, chloride axial -7.63, methyl axial -8.96.
-
-
-
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32
-
-
5344228543
-
-
note
-
Another boat conformer with the stereogenic methyl occupying a pseudoaxial site could not be found.
-
-
-
-
33
-
-
85088619337
-
-
note
-
11B NMR: see ref 19b.
-
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-
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34
-
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85088620916
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note
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3 (bp 12.5 °C).
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35
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0000144120
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See, for example: (a) Keck, G E.; Castellino, S. J. Am. Chem. Soc. 1986, 108, 3847-3849. (b) Keck, G. E.; Castellino, S.; Wiley, M. R. J. Org Chem. 1986, 51, 5480-5482. (c) Keck, G. E.; Castellino, S. Tetrahedron Lett. 1987, 28, 281-284.
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See, for example: (a) Keck, G E.; Castellino, S. J. Am. Chem. Soc. 1986, 108, 3847-3849. (b) Keck, G. E.; Castellino, S.; Wiley, M. R. J. Org Chem. 1986, 51, 5480-5482. (c) Keck, G. E.; Castellino, S. Tetrahedron Lett. 1987, 28, 281-284.
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See, for example: (a) Keck, G E.; Castellino, S. J. Am. Chem. Soc. 1986, 108, 3847-3849. (b) Keck, G. E.; Castellino, S.; Wiley, M. R. J. Org Chem. 1986, 51, 5480-5482. (c) Keck, G. E.; Castellino, S. Tetrahedron Lett. 1987, 28, 281-284.
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5344223574
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note
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See Experimental Section for more details.
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39
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85088621353
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note
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3 at rt. Our experience is that chemical shifts of such compounds are not greatly dependent on temperature or the chlorinated solvent used.
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41
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0003942864
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5344274737
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note
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Six hours of stirring is sufficient at this point. If an ester is present in the substrate, transesterification has been observed with the longer reaction time.
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