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85033143045
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note
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The α-silylketone might undergo Brook rearrangement, although we have not isolated the corresponding silyl enol ether. The parent vinylketone is sometimes present in small amount as a byproduct and could be formed either through desilylation of 10 or hydrolysis of a silyl enol ether.
-
-
-
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78
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49549150557
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For metallo-carbene insertion into N-H bonds: see: (a) Paulissen, R.; Hayez, E.; Hubert, A. J.; Teyssié, P. Tetrahedron Lett. 1974, 607. (b) Nicoud, J.-F.; Kagan, H. Tetrahedron Lett. 1971, 2065. O-H bonds: (a) Cox, G. C.; Miller, D. J.; Moody, C. J.; Sie, E.-R.H.B.; Kulagowski, J. J. Tetrahedron 1994, 50, 3195. (c) Haigh, D. Tetrahedron 1994, 50, 3177. (c) Aller, E.; Cox, G. G.; Miller, D. J.; Moody, C. J. Tetrahedron Lett. 1994, 35, 5949. (d) Landais, Y.; Planchenault, D. Synlett 1995, 1191. (e) Cox, G. G.; Moody, C. J.; Austin, D. J.; Padwa, A. Tetrahedron 1993, 49, 5109.
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Paulissen, R.1
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0002234495
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For metallo-carbene insertion into N-H bonds: see: (a) Paulissen, R.; Hayez, E.; Hubert, A. J.; Teyssié, P. Tetrahedron Lett. 1974, 607. (b) Nicoud, J.-F.; Kagan, H. Tetrahedron Lett. 1971, 2065. O-H bonds: (a) Cox, G. C.; Miller, D. J.; Moody, C. J.; Sie, E.-R.H.B.; Kulagowski, J. J. Tetrahedron 1994, 50, 3195. (c) Haigh, D. Tetrahedron 1994, 50, 3177. (c) Aller, E.; Cox, G. G.; Miller, D. J.; Moody, C. J. Tetrahedron Lett. 1994, 35, 5949. (d) Landais, Y.; Planchenault, D. Synlett 1995, 1191. (e) Cox, G. G.; Moody, C. J.; Austin, D. J.; Padwa, A. Tetrahedron 1993, 49, 5109.
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For metallo-carbene insertion into N-H bonds: see: (a) Paulissen, R.; Hayez, E.; Hubert, A. J.; Teyssié, P. Tetrahedron Lett. 1974, 607. (b) Nicoud, J.-F.; Kagan, H. Tetrahedron Lett. 1971, 2065. O-H bonds: (a) Cox, G. C.; Miller, D. J.; Moody, C. J.; Sie, E.-R.H.B.; Kulagowski, J. J. Tetrahedron 1994, 50, 3195. (c) Haigh, D. Tetrahedron 1994, 50, 3177. (c) Aller, E.; Cox, G. G.; Miller, D. J.; Moody, C. J. Tetrahedron Lett. 1994, 35, 5949. (d) Landais, Y.; Planchenault, D. Synlett 1995, 1191. (e) Cox, G. G.; Moody, C. J.; Austin, D. J.; Padwa, A. Tetrahedron 1993, 49, 5109.
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For metallo-carbene insertion into N-H bonds: see: (a) Paulissen, R.; Hayez, E.; Hubert, A. J.; Teyssié, P. Tetrahedron Lett. 1974, 607. (b) Nicoud, J.-F.; Kagan, H. Tetrahedron Lett. 1971, 2065. O-H bonds: (a) Cox, G. C.; Miller, D. J.; Moody, C. J.; Sie, E.-R.H.B.; Kulagowski, J. J. Tetrahedron 1994, 50, 3195. (c) Haigh, D. Tetrahedron 1994, 50, 3177. (c) Aller, E.; Cox, G. G.; Miller, D. J.; Moody, C. J. Tetrahedron Lett. 1994, 35, 5949. (d) Landais, Y.; Planchenault, D. Synlett 1995, 1191. (e) Cox, G. G.; Moody, C. J.; Austin, D. J.; Padwa, A. Tetrahedron 1993, 49, 5109.
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For metallo-carbene insertion into N-H bonds: see: (a) Paulissen, R.; Hayez, E.; Hubert, A. J.; Teyssié, P. Tetrahedron Lett. 1974, 607. (b) Nicoud, J.-F.; Kagan, H. Tetrahedron Lett. 1971, 2065. O-H bonds: (a) Cox, G. C.; Miller, D. J.; Moody, C. J.; Sie, E.-R.H.B.; Kulagowski, J. J. Tetrahedron 1994, 50, 3195. (c) Haigh, D. Tetrahedron 1994, 50, 3177. (c) Aller, E.; Cox, G. G.; Miller, D. J.; Moody, C. J. Tetrahedron Lett. 1994, 35, 5949. (d) Landais, Y.; Planchenault, D. Synlett 1995, 1191. (e) Cox, G. G.; Moody, C. J.; Austin, D. J.; Padwa, A. Tetrahedron 1993, 49, 5109.
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For metallo-carbene insertion into N-H bonds: see: (a) Paulissen, R.; Hayez, E.; Hubert, A. J.; Teyssié, P. Tetrahedron Lett. 1974, 607. (b) Nicoud, J.-F.; Kagan, H. Tetrahedron Lett. 1971, 2065. O-H bonds: (a) Cox, G. C.; Miller, D. J.; Moody, C. J.; Sie, E.-R.H.B.; Kulagowski, J. J. Tetrahedron 1994, 50, 3195. (c) Haigh, D. Tetrahedron 1994, 50, 3177. (c) Aller, E.; Cox, G. G.; Miller, D. J.; Moody, C. J. Tetrahedron Lett. 1994, 35, 5949. (d) Landais, Y.; Planchenault, D. Synlett 1995, 1191. (e) Cox, G. G.; Moody, C. J.; Austin, D. J.; Padwa, A. Tetrahedron 1993, 49, 5109.
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A 30-50% isomerization of the double bond was observed under these conditions with the (Z)-hex-3-enoic acid.
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note
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Hydrogenation of the double bond of 19c and 19d led to products with the same configuration, indicating that the topicity of the insertion reaction was identical for (E) and (Z)-diazo precursors.
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85033150932
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note
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31c 23b was assumed to possess the same absolute configuration as 23a.
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110
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85033152922
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03-29- Gwatt (Switzerland)
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A preliminary account of these results has been presented: Chiral 2 symposium, (03-29-1995), Gwatt (Switzerland).
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For other asymmetric routes to α-silylcarbonyl compounds, see: (a) Enders, D.; Nakai, S. Helv. Chim. Acta 1990, 73, 1833. (b) Enders, D.; Nakai, S. Chem. Ber. 1991, 24, 219. (c) Bhushan, V.; Lohray, B. B.; Enders, D. Tetrahedron Lett. 1993, 34, 5067.
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84985727190
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For other asymmetric routes to α-silylcarbonyl compounds, see: (a) Enders, D.; Nakai, S. Helv. Chim. Acta 1990, 73, 1833. (b) Enders, D.; Nakai, S. Chem. Ber. 1991, 24, 219. (c) Bhushan, V.; Lohray, B. B.; Enders, D. Tetrahedron Lett. 1993, 34, 5067.
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For other asymmetric routes to α-silylcarbonyl compounds, see: (a) Enders, D.; Nakai, S. Helv. Chim. Acta 1990, 73, 1833. (b) Enders, D.; Nakai, S. Chem. Ber. 1991, 24, 219. (c) Bhushan, V.; Lohray, B. B.; Enders, D. Tetrahedron Lett. 1993, 34, 5067.
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(e) Le Bideau, F.; Gilloir, F.; Nilsson, Y.; Aubert, C.; Malacria, M. Tetrahedron Lett. 1995, 36, 1641.
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While this work was submitted, an article on asymmetric Si-H insertion of phenyldiazoacetate appeared, reporting enantioselectivities of up to 50%, see: Buck, R. T.; Doyle, M. P.; Drysdale, M. J.; Ferris, L.; Forbes, D. C.; Haigh, D.; Moody, C. J.; Pearson, N. D.; Zhou, Q.-L. Tetrahedron Lett. 1996, 37, 7631.
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