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Hydrosilylation of ketones catalyzed by C2-symmetric proline-derived complexes
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| Zeitschriftentitel: | Canadian Journal of Chemistry |
|---|---|
| Personen und Körperschaften: | , |
| In: | Canadian Journal of Chemistry, 84, 2006, 10, S. 1416-1425 |
| Format: | E-Article |
| Sprache: | Englisch |
| veröffentlicht: |
Canadian Science Publishing
|
| Schlagwörter: |
| author_facet |
Gan, Li Brook, Michael A Gan, Li Brook, Michael A |
|---|---|
| author |
Gan, Li Brook, Michael A |
| spellingShingle |
Gan, Li Brook, Michael A Canadian Journal of Chemistry Hydrosilylation of ketones catalyzed by C2-symmetric proline-derived complexes Organic Chemistry General Chemistry Catalysis |
| author_sort |
gan, li |
| spelling |
Gan, Li Brook, Michael A 0008-4042 1480-3291 Canadian Science Publishing Organic Chemistry General Chemistry Catalysis http://dx.doi.org/10.1139/v06-116 <jats:p> Extracoordinate chiral hydrosilanes were generated in situ from triethoxysilane and a C<jats:sub>2</jats:sub>-symmetric ligand derived from bisproline 7. In the presence of a catalytic amount of ligand 7, prochiral ketones were reduced in moderate yield with moderate enantioselectivity (up to 64% ee). Alternatively, TiF<jats:sub>4</jats:sub> complexes of 7 were used to provide higher enantioselectivity and with improved yields. The copper complex of ligand 7 and <jats:sup>29</jats:sup>Si NMR data provide some guidance as to the key factors responsible for the observed reactivity at the silicon and at the ligand centre.Key words: extracoordinate chiral silane, C<jats:sub>2</jats:sub>-symmetry, enantioselectivity, Lewis acid titanium catalysis. </jats:p> Hydrosilylation of ketones catalyzed by <i>C</i><sub>2</sub>-symmetric proline-derived complexes Canadian Journal of Chemistry |
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Canadian Science Publishing, 2006 |
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| title |
Hydrosilylation of ketones catalyzed by C2-symmetric proline-derived complexes |
| title_unstemmed |
Hydrosilylation of ketones catalyzed by C2-symmetric proline-derived complexes |
| title_full |
Hydrosilylation of ketones catalyzed by C2-symmetric proline-derived complexes |
| title_fullStr |
Hydrosilylation of ketones catalyzed by C2-symmetric proline-derived complexes |
| title_full_unstemmed |
Hydrosilylation of ketones catalyzed by C2-symmetric proline-derived complexes |
| title_short |
Hydrosilylation of ketones catalyzed by C2-symmetric proline-derived complexes |
| title_sort |
hydrosilylation of ketones catalyzed by <i>c</i><sub>2</sub>-symmetric proline-derived complexes |
| topic |
Organic Chemistry General Chemistry Catalysis |
| url |
http://dx.doi.org/10.1139/v06-116 |
| publishDate |
2006 |
| physical |
1416-1425 |
| description |
<jats:p> Extracoordinate chiral hydrosilanes were generated in situ from triethoxysilane and a C<jats:sub>2</jats:sub>-symmetric ligand derived from bisproline 7. In the presence of a catalytic amount of ligand 7, prochiral ketones were reduced in moderate yield with moderate enantioselectivity (up to 64% ee). Alternatively, TiF<jats:sub>4</jats:sub> complexes of 7 were used to provide higher enantioselectivity and with improved yields. The copper complex of ligand 7 and <jats:sup>29</jats:sup>Si NMR data provide some guidance as to the key factors responsible for the observed reactivity at the silicon and at the ligand centre.Key words: extracoordinate chiral silane, C<jats:sub>2</jats:sub>-symmetry, enantioselectivity, Lewis acid titanium catalysis. </jats:p> |
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| author | Gan, Li, Brook, Michael A |
| author_facet | Gan, Li, Brook, Michael A, Gan, Li, Brook, Michael A |
| author_sort | gan, li |
| container_issue | 10 |
| container_start_page | 1416 |
| container_title | Canadian Journal of Chemistry |
| container_volume | 84 |
| description | <jats:p> Extracoordinate chiral hydrosilanes were generated in situ from triethoxysilane and a C<jats:sub>2</jats:sub>-symmetric ligand derived from bisproline 7. In the presence of a catalytic amount of ligand 7, prochiral ketones were reduced in moderate yield with moderate enantioselectivity (up to 64% ee). Alternatively, TiF<jats:sub>4</jats:sub> complexes of 7 were used to provide higher enantioselectivity and with improved yields. The copper complex of ligand 7 and <jats:sup>29</jats:sup>Si NMR data provide some guidance as to the key factors responsible for the observed reactivity at the silicon and at the ligand centre.Key words: extracoordinate chiral silane, C<jats:sub>2</jats:sub>-symmetry, enantioselectivity, Lewis acid titanium catalysis. </jats:p> |
| doi_str_mv | 10.1139/v06-116 |
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| spelling | Gan, Li Brook, Michael A 0008-4042 1480-3291 Canadian Science Publishing Organic Chemistry General Chemistry Catalysis http://dx.doi.org/10.1139/v06-116 <jats:p> Extracoordinate chiral hydrosilanes were generated in situ from triethoxysilane and a C<jats:sub>2</jats:sub>-symmetric ligand derived from bisproline 7. In the presence of a catalytic amount of ligand 7, prochiral ketones were reduced in moderate yield with moderate enantioselectivity (up to 64% ee). Alternatively, TiF<jats:sub>4</jats:sub> complexes of 7 were used to provide higher enantioselectivity and with improved yields. The copper complex of ligand 7 and <jats:sup>29</jats:sup>Si NMR data provide some guidance as to the key factors responsible for the observed reactivity at the silicon and at the ligand centre.Key words: extracoordinate chiral silane, C<jats:sub>2</jats:sub>-symmetry, enantioselectivity, Lewis acid titanium catalysis. </jats:p> Hydrosilylation of ketones catalyzed by <i>C</i><sub>2</sub>-symmetric proline-derived complexes Canadian Journal of Chemistry |
| spellingShingle | Gan, Li, Brook, Michael A, Canadian Journal of Chemistry, Hydrosilylation of ketones catalyzed by C2-symmetric proline-derived complexes, Organic Chemistry, General Chemistry, Catalysis |
| title | Hydrosilylation of ketones catalyzed by C2-symmetric proline-derived complexes |
| title_full | Hydrosilylation of ketones catalyzed by C2-symmetric proline-derived complexes |
| title_fullStr | Hydrosilylation of ketones catalyzed by C2-symmetric proline-derived complexes |
| title_full_unstemmed | Hydrosilylation of ketones catalyzed by C2-symmetric proline-derived complexes |
| title_short | Hydrosilylation of ketones catalyzed by C2-symmetric proline-derived complexes |
| title_sort | hydrosilylation of ketones catalyzed by <i>c</i><sub>2</sub>-symmetric proline-derived complexes |
| title_unstemmed | Hydrosilylation of ketones catalyzed by C2-symmetric proline-derived complexes |
| topic | Organic Chemistry, General Chemistry, Catalysis |
| url | http://dx.doi.org/10.1139/v06-116 |