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Volumn 62, Issue 6, 1997, Pages 1630-1641

A Stereospecific Access to Allylic Systems Using Rhodium(II)-Vinyl Carbenoid Insertion into Si-H, O-H, and N-H Bonds

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EID: 0000558907     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo961952j     Document Type: Article
Times cited : (116)

References (123)
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    • 3 group can also be carried out, albeit in modest yield, see: Smitrovich, J.-H.; Woerpel, K. A. J. Org. Chem. 1996, 61, 6044.
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    • note
    • 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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    • 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.
    • (1974) Tetrahedron Lett. , pp. 607
    • Paulissen, R.1    Hayez, E.2    Hubert, A.J.3    Teyssié, P.4
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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.
    • (1971) Tetrahedron Lett. , pp. 2065
    • Nicoud, J.-F.1    Kagan, H.2
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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.
    • (1994) Tetrahedron , vol.50 , pp. 3195
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  • 81
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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.
    • (1994) Tetrahedron , vol.50 , pp. 3177
    • Haigh, D.1
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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.
    • (1994) Tetrahedron Lett. , vol.35 , pp. 5949
    • Aller, E.1    Cox, G.G.2    Miller, D.J.3    Moody, C.J.4
  • 83
    • 85064868152 scopus 로고
    • 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.
    • (1995) Synlett , pp. 1191
    • Landais, Y.1    Planchenault, D.2
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    • 0027287678 scopus 로고
    • 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.
    • (1993) Tetrahedron , vol.49 , pp. 5109
    • Cox, G.G.1    Moody, C.J.2    Austin, D.J.3    Padwa, A.4
  • 85
  • 95
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    • note
    • A 30-50% isomerization of the double bond was observed under these conditions with the (Z)-hex-3-enoic acid.
  • 101
    • 85033154369 scopus 로고    scopus 로고
    • note
    • 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.
  • 109
    • 85033150932 scopus 로고    scopus 로고
    • note
    • 31c 23b was assumed to possess the same absolute configuration as 23a.
  • 110
    • 85033152922 scopus 로고
    • 03-29- Gwatt (Switzerland)
    • A preliminary account of these results has been presented: Chiral 2 symposium, (03-29-1995), Gwatt (Switzerland).
    • (1995) Chiral 2 Symposium , vol.2
  • 111
    • 1542608503 scopus 로고
    • 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.
    • (1990) Helv. Chim. Acta , vol.73 , pp. 1833
    • Nakai, S.1
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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.
    • (1991) Chem. Ber. , vol.24 , pp. 219
    • Enders, D.1    Nakai, S.2
  • 113
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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.
    • (1993) Tetrahedron Lett. , vol.34 , pp. 5067
    • Bhushan, V.1    Lohray, B.B.2    Enders, D.3


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