The preparation of trans-2,5- dialkylpyrrolidinylbenzyldiphenylphosphines: New phosphinamine ligands for asymmetric catalysis

Tetrahedron Asymmetry

Volumn 9, Issue 21, 1998, Pages 3831-3839

  Cahill, John P ^a   Bohnen, Frank M ^b   Goddard, Richard ^b   Krüger, Carl ^b   Guiry, Patrick J ^a  

^a UNIVERSITY COLLEGE DUBLIN   (Ireland)

^b MAX PLANCK INSTITUT FÜR KOHLENFORSCHUNG   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

LIGAND; PHOSPHINE DERIVATIVE;

ARTICLE; CATALYSIS; CRYSTAL STRUCTURE; CYCLIZATION; ENANTIOMER; POLYMERIZATION; PRIORITY JOURNAL; PROTON NUCLEAR MAGNETIC RESONANCE; X RAY CRYSTALLOGRAPHY;

EID: 0032491618     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0957-4166(98)00393-0     Document Type: Article

References (41)

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2. Allylic Substitutions: Reviews: (a) Frost, C. G.; Howarth, J.; Williams, J. M. J. Tetrahedron: Asymmetry 1992, 3, 1089. (b) Hayashi, T. In Catalytic Asymmetric Synthesis; Ojima, I., Ed.; VCH: Weinheim, 1993. (c) Trost, B. M.; Van Dranken, D. L. Chem. Rev. 1996, 96, 395. Selected papers: (d) Togni, A.; Burckhardt, U.; Gramlich, V.; Pregosin, P.; Salzmann, R. J. Am. Chem. Soc. 1996, 118, 1031. (e) Brown, J. M.; Hulmes, D. I.; Guiry, P. J. Tetrahedron 1994, 50, 4493. (f) Zhang, W.; Hirao, T.; Ikeda, I. Tetrahedron Lett. 1996, 37, 4545. (g) Ahn, K. H.; Cho, C.- W.; Park, J.; Lee, S. Tetrahedron: Asymmetry 1997, 8, 1179. (h) Wiese, B.; Helmchen, G. Tetrahedron Lett. 1998, 39, 5727. (i) Lloyd-Jones, G. C.; Pfaltz, A. Angew. Chem., Int. Ed. Engl. 1995, 34, 462.
3. Allylic Substitutions: Reviews: (a) Frost, C. G.; Howarth, J.; Williams, J. M. J. Tetrahedron: Asymmetry 1992, 3, 1089. (b) Hayashi, T. In Catalytic Asymmetric Synthesis; Ojima, I., Ed.; VCH: Weinheim, 1993. (c) Trost, B. M.; Van Dranken, D. L. Chem. Rev. 1996, 96, 395. Selected papers: (d) Togni, A.; Burckhardt, U.; Gramlich, V.; Pregosin, P.; Salzmann, R. J. Am. Chem. Soc. 1996, 118, 1031. (e) Brown, J. M.; Hulmes, D. I.; Guiry, P. J. Tetrahedron 1994, 50, 4493. (f) Zhang, W.; Hirao, T.; Ikeda, I. Tetrahedron Lett. 1996, 37, 4545. (g) Ahn, K. H.; Cho, C.- W.; Park, J.; Lee, S. Tetrahedron: Asymmetry 1997, 8, 1179. (h) Wiese, B.; Helmchen, G. Tetrahedron Lett. 1998, 39, 5727. (i) Lloyd-Jones, G. C.; Pfaltz, A. Angew. Chem., Int. Ed. Engl. 1995, 34, 462.
4. Allylic Substitutions: Reviews: (a) Frost, C. G.; Howarth, J.; Williams, J. M. J. Tetrahedron: Asymmetry 1992, 3, 1089. (b) Hayashi, T. In Catalytic Asymmetric Synthesis; Ojima, I., Ed.; VCH: Weinheim, 1993. (c) Trost, B. M.; Van Dranken, D. L. Chem. Rev. 1996, 96, 395. Selected papers: (d) Togni, A.; Burckhardt, U.; Gramlich, V.; Pregosin, P.; Salzmann, R. J. Am. Chem. Soc. 1996, 118, 1031. (e) Brown, J. M.; Hulmes, D. I.; Guiry, P. J. Tetrahedron 1994, 50, 4493. (f) Zhang, W.; Hirao, T.; Ikeda, I. Tetrahedron Lett. 1996, 37, 4545. (g) Ahn, K. H.; Cho, C.- W.; Park, J.; Lee, S. Tetrahedron: Asymmetry 1997, 8, 1179. (h) Wiese, B.; Helmchen, G. Tetrahedron Lett. 1998, 39, 5727. (i) Lloyd-Jones, G. C.; Pfaltz, A. Angew. Chem., Int. Ed. Engl. 1995, 34, 462.
5. Allylic Substitutions: Reviews: (a) Frost, C. G.; Howarth, J.; Williams, J. M. J. Tetrahedron: Asymmetry 1992, 3, 1089. (b) Hayashi, T. In Catalytic Asymmetric Synthesis; Ojima, I., Ed.; VCH: Weinheim, 1993. (c) Trost, B. M.; Van Dranken, D. L. Chem. Rev. 1996, 96, 395. Selected papers: (d) Togni, A.; Burckhardt, U.; Gramlich, V.; Pregosin, P.; Salzmann, R. J. Am. Chem. Soc. 1996, 118, 1031. (e) Brown, J. M.; Hulmes, D. I.; Guiry, P. J. Tetrahedron 1994, 50, 4493. (f) Zhang, W.; Hirao, T.; Ikeda, I. Tetrahedron Lett. 1996, 37, 4545. (g) Ahn, K. H.; Cho, C.- W.; Park, J.; Lee, S. Tetrahedron: Asymmetry 1997, 8, 1179. (h) Wiese, B.; Helmchen, G. Tetrahedron Lett. 1998, 39, 5727. (i) Lloyd-Jones, G. C.; Pfaltz, A. Angew. Chem., Int. Ed. Engl. 1995, 34, 462.
6. Allylic Substitutions: Reviews: (a) Frost, C. G.; Howarth, J.; Williams, J. M. J. Tetrahedron: Asymmetry 1992, 3, 1089. (b) Hayashi, T. In Catalytic Asymmetric Synthesis; Ojima, I., Ed.; VCH: Weinheim, 1993. (c) Trost, B. M.; Van Dranken, D. L. Chem. Rev. 1996, 96, 395. Selected papers: (d) Togni, A.; Burckhardt, U.; Gramlich, V.; Pregosin, P.; Salzmann, R. J. Am. Chem. Soc. 1996, 118, 1031. (e) Brown, J. M.; Hulmes, D. I.; Guiry, P. J. Tetrahedron 1994, 50, 4493. (f) Zhang, W.; Hirao, T.; Ikeda, I. Tetrahedron Lett. 1996, 37, 4545. (g) Ahn, K. H.; Cho, C.- W.; Park, J.; Lee, S. Tetrahedron: Asymmetry 1997, 8, 1179. (h) Wiese, B.; Helmchen, G. Tetrahedron Lett. 1998, 39, 5727. (i) Lloyd-Jones, G. C.; Pfaltz, A. Angew. Chem., Int. Ed. Engl. 1995, 34, 462.
7. Allylic Substitutions: Reviews: (a) Frost, C. G.; Howarth, J.; Williams, J. M. J. Tetrahedron: Asymmetry 1992, 3, 1089. (b) Hayashi, T. In Catalytic Asymmetric Synthesis; Ojima, I., Ed.; VCH: Weinheim, 1993. (c) Trost, B. M.; Van Dranken, D. L. Chem. Rev. 1996, 96, 395. Selected papers: (d) Togni, A.; Burckhardt, U.; Gramlich, V.; Pregosin, P.; Salzmann, R. J. Am. Chem. Soc. 1996, 118, 1031. (e) Brown, J. M.; Hulmes, D. I.; Guiry, P. J. Tetrahedron 1994, 50, 4493. (f) Zhang, W.; Hirao, T.; Ikeda, I. Tetrahedron Lett. 1996, 37, 4545. (g) Ahn, K. H.; Cho, C.- W.; Park, J.; Lee, S. Tetrahedron: Asymmetry 1997, 8, 1179. (h) Wiese, B.; Helmchen, G. Tetrahedron Lett. 1998, 39, 5727. (i) Lloyd-Jones, G. C.; Pfaltz, A. Angew. Chem., Int. Ed. Engl. 1995, 34, 462.
8. Allylic Substitutions: Reviews: (a) Frost, C. G.; Howarth, J.; Williams, J. M. J. Tetrahedron: Asymmetry 1992, 3, 1089. (b) Hayashi, T. In Catalytic Asymmetric Synthesis; Ojima, I., Ed.; VCH: Weinheim, 1993. (c) Trost, B. M.; Van Dranken, D. L. Chem. Rev. 1996, 96, 395. Selected papers: (d) Togni, A.; Burckhardt, U.; Gramlich, V.; Pregosin, P.; Salzmann, R. J. Am. Chem. Soc. 1996, 118, 1031. (e) Brown, J. M.; Hulmes, D. I.; Guiry, P. J. Tetrahedron 1994, 50, 4493. (f) Zhang, W.; Hirao, T.; Ikeda, I. Tetrahedron Lett. 1996, 37, 4545. (g) Ahn, K. H.; Cho, C.- W.; Park, J.; Lee, S. Tetrahedron: Asymmetry 1997, 8, 1179. (h) Wiese, B.; Helmchen, G. Tetrahedron Lett. 1998, 39, 5727. (i) Lloyd-Jones, G. C.; Pfaltz, A. Angew. Chem., Int. Ed. Engl. 1995, 34, 462.
9. Allylic Substitutions: Reviews: (a) Frost, C. G.; Howarth, J.; Williams, J. M. J. Tetrahedron: Asymmetry 1992, 3, 1089. (b) Hayashi, T. In Catalytic Asymmetric Synthesis; Ojima, I., Ed.; VCH: Weinheim, 1993. (c) Trost, B. M.; Van Dranken, D. L. Chem. Rev. 1996, 96, 395. Selected papers: (d) Togni, A.; Burckhardt, U.; Gramlich, V.; Pregosin, P.; Salzmann, R. J. Am. Chem. Soc. 1996, 118, 1031. (e) Brown, J. M.; Hulmes, D. I.; Guiry, P. J. Tetrahedron 1994, 50, 4493. (f) Zhang, W.; Hirao, T.; Ikeda, I. Tetrahedron Lett. 1996, 37, 4545. (g) Ahn, K. H.; Cho, C.- W.; Park, J.; Lee, S. Tetrahedron: Asymmetry 1997, 8, 1179. (h) Wiese, B.; Helmchen, G. Tetrahedron Lett. 1998, 39, 5727. (i) Lloyd-Jones, G. C.; Pfaltz, A. Angew. Chem., Int. Ed. Engl. 1995, 34, 462.
10. Hydrosilylations: Selected papers: (a) Newman, L. M.; Williams, J. M. J.; McCague, R.; Potter, G. A. Tetrahedron: Asymmetry 1996, 6, 1597. (b) Langer, T.; Janssen, J.; Helmchen, G. Tetrahedron: Asymmetry 1996, 6, 1599. (c) Uemura, S.; Nishibayashi, Y.; Segawa, K.; Ohe, K. Organometallics 1995, 14, 5486. Hydroborations: selected papers: (a) Brown, J. M.; Hulmes, D. I.; Layzell, T. P. J. Chem. Soc., Chem. Commun. 1993, 1673. (b) Valk, J.-M.; Whitlock, G. A.; Layzell, T. P.; Brown, J. M. Tetrahedron: Asymmetry 1995, 6, 2593. (c) Schnyder, A.; Hintermann, L.; Togni, A. Angew. Chem., Int. Ed. Engl. 1995, 34, 931. (d) Review: Beletskaya, I.; Pelter, A. Tetrahedron 1997, 57, 4957.
11. Hydrosilylations: Selected papers: (a) Newman, L. M.; Williams, J. M. J.; McCague, R.; Potter, G. A. Tetrahedron: Asymmetry 1996, 6, 1597. (b) Langer, T.; Janssen, J.; Helmchen, G. Tetrahedron: Asymmetry 1996, 6, 1599. (c) Uemura, S.; Nishibayashi, Y.; Segawa, K.; Ohe, K. Organometallics 1995, 14, 5486. Hydroborations: selected papers: (a) Brown, J. M.; Hulmes, D. I.; Layzell, T. P. J. Chem. Soc., Chem. Commun. 1993, 1673. (b) Valk, J.-M.; Whitlock, G. A.; Layzell, T. P.; Brown, J. M. Tetrahedron: Asymmetry 1995, 6, 2593. (c) Schnyder, A.; Hintermann, L.; Togni, A. Angew. Chem., Int. Ed. Engl. 1995, 34, 931. (d) Review: Beletskaya, I.; Pelter, A. Tetrahedron 1997, 57, 4957.
12. Hydrosilylations: Selected papers: (a) Newman, L. M.; Williams, J. M. J.; McCague, R.; Potter, G. A. Tetrahedron: Asymmetry 1996, 6, 1597. (b) Langer, T.; Janssen, J.; Helmchen, G. Tetrahedron: Asymmetry 1996, 6, 1599. (c) Uemura, S.; Nishibayashi, Y.; Segawa, K.; Ohe, K. Organometallics 1995, 14, 5486. Hydroborations: selected papers: (a) Brown, J. M.; Hulmes, D. I.; Layzell, T. P. J. Chem. Soc., Chem. Commun. 1993, 1673. (b) Valk, J.-M.; Whitlock, G. A.; Layzell, T. P.; Brown, J. M. Tetrahedron: Asymmetry 1995, 6, 2593. (c) Schnyder, A.; Hintermann, L.; Togni, A. Angew. Chem., Int. Ed. Engl. 1995, 34, 931. (d) Review: Beletskaya, I.; Pelter, A. Tetrahedron 1997, 57, 4957.
13. Hydrosilylations: Selected papers: (a) Newman, L. M.; Williams, J. M. J.; McCague, R.; Potter, G. A. Tetrahedron: Asymmetry 1996, 6, 1597. (b) Langer, T.; Janssen, J.; Helmchen, G. Tetrahedron: Asymmetry 1996, 6, 1599. (c) Uemura, S.; Nishibayashi, Y.; Segawa, K.; Ohe, K. Organometallics 1995, 14, 5486. Hydroborations: selected papers: (a) Brown, J. M.; Hulmes, D. I.; Layzell, T. P. J. Chem. Soc., Chem. Commun. 1993, 1673. (b) Valk, J.-M.; Whitlock, G. A.; Layzell, T. P.; Brown, J. M. Tetrahedron: Asymmetry 1995, 6, 2593. (c) Schnyder, A.; Hintermann, L.; Togni, A. Angew. Chem., Int. Ed. Engl. 1995, 34, 931. (d) Review: Beletskaya, I.; Pelter, A. Tetrahedron 1997, 57, 4957.
14. Hydrosilylations: Selected papers: (a) Newman, L. M.; Williams, J. M. J.; McCague, R.; Potter, G. A. Tetrahedron: Asymmetry 1996, 6, 1597. (b) Langer, T.; Janssen, J.; Helmchen, G. Tetrahedron: Asymmetry 1996, 6, 1599. (c) Uemura, S.; Nishibayashi, Y.; Segawa, K.; Ohe, K. Organometallics 1995, 14, 5486. Hydroborations: selected papers: (a) Brown, J. M.; Hulmes, D. I.; Layzell, T. P. J. Chem. Soc., Chem. Commun. 1993, 1673. (b) Valk, J.-M.; Whitlock, G. A.; Layzell, T. P.; Brown, J. M. Tetrahedron: Asymmetry 1995, 6, 2593. (c) Schnyder, A.; Hintermann, L.; Togni, A. Angew. Chem., Int. Ed. Engl. 1995, 34, 931. (d) Review: Beletskaya, I.; Pelter, A. Tetrahedron 1997, 57, 4957.
15. Hydrosilylations: Selected papers: (a) Newman, L. M.; Williams, J. M. J.; McCague, R.; Potter, G. A. Tetrahedron: Asymmetry 1996, 6, 1597. (b) Langer, T.; Janssen, J.; Helmchen, G. Tetrahedron: Asymmetry 1996, 6, 1599. (c) Uemura, S.; Nishibayashi, Y.; Segawa, K.; Ohe, K. Organometallics 1995, 14, 5486. Hydroborations: selected papers: (a) Brown, J. M.; Hulmes, D. I.; Layzell, T. P. J. Chem. Soc., Chem. Commun. 1993, 1673. (b) Valk, J.-M.; Whitlock, G. A.; Layzell, T. P.; Brown, J. M. Tetrahedron: Asymmetry 1995, 6, 2593. (c) Schnyder, A.; Hintermann, L.; Togni, A. Angew. Chem., Int. Ed. Engl. 1995, 34, 931. (d) Review: Beletskaya, I.; Pelter, A. Tetrahedron 1997, 57, 4957.
16. Hydrosilylations: Selected papers: (a) Newman, L. M.; Williams, J. M. J.; McCague, R.; Potter, G. A. Tetrahedron: Asymmetry 1996, 6, 1597. (b) Langer, T.; Janssen, J.; Helmchen, G. Tetrahedron: Asymmetry 1996, 6, 1599. (c) Uemura, S.; Nishibayashi, Y.; Segawa, K.; Ohe, K. Organometallics 1995, 14, 5486. Hydroborations: selected papers: (a) Brown, J. M.; Hulmes, D. I.; Layzell, T. P. J. Chem. Soc., Chem. Commun. 1993, 1673. (b) Valk, J.-M.; Whitlock, G. A.; Layzell, T. P.; Brown, J. M. Tetrahedron: Asymmetry 1995, 6, 2593. (c) Schnyder, A.; Hintermann, L.; Togni, A. Angew. Chem., Int. Ed. Engl. 1995, 34, 931. (d) Review: Beletskaya, I.; Pelter, A. Tetrahedron 1997, 57, 4957.
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