Precise structure activity relationships in asymmetric catalysis using carbohydrate scaffolds to allow ready fine tuning: dialkylzinc-aldehyde additions.
The ready construction of 24 stereochemically and functionally diverse carbohydrate ligand structures from a core D-glucosamine scaffold has allowed the evaluation of broad ranging structure activity relationships in ligand accelerated zincate additions to aldehydes, with variations in deltadeltaG+/...
| Main Authors: | , , , , , , , |
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| Format: | Journal article |
| Language: | English |
| Published: |
2003
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| _version_ | 1826287214295777280 |
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| author | Emmerson, D Villard, R Mugnaini, C Batsanov, A Howard, J Hems, W Tooze, R Davis, B |
| author_facet | Emmerson, D Villard, R Mugnaini, C Batsanov, A Howard, J Hems, W Tooze, R Davis, B |
| author_sort | Emmerson, D |
| collection | OXFORD |
| description | The ready construction of 24 stereochemically and functionally diverse carbohydrate ligand structures from a core D-glucosamine scaffold has allowed the evaluation of broad ranging structure activity relationships in ligand accelerated zincate additions to aldehydes, with variations in deltadeltaG+/+(R-S) of up to 5650 J mol(-1) that create opposing senses of asymmetric induction and that are consistent with models based on several ligand X-ray structures and molecular mechanics analysis. Factorial analysis of enantioselectivity using key dihedral angles and steric volume on N-2 also highlight the potential for the use of factorial design in ligand construction. |
| first_indexed | 2024-03-07T01:55:16Z |
| format | Journal article |
| id | oxford-uuid:9b7d65c5-0de7-4037-ad55-5ebf68511371 |
| institution | University of Oxford |
| language | English |
| last_indexed | 2024-03-07T01:55:16Z |
| publishDate | 2003 |
| record_format | dspace |
| spelling | oxford-uuid:9b7d65c5-0de7-4037-ad55-5ebf685113712022-03-27T00:29:13ZPrecise structure activity relationships in asymmetric catalysis using carbohydrate scaffolds to allow ready fine tuning: dialkylzinc-aldehyde additions.Journal articlehttp://purl.org/coar/resource_type/c_dcae04bcuuid:9b7d65c5-0de7-4037-ad55-5ebf68511371EnglishSymplectic Elements at Oxford2003Emmerson, DVillard, RMugnaini, CBatsanov, AHoward, JHems, WTooze, RDavis, BThe ready construction of 24 stereochemically and functionally diverse carbohydrate ligand structures from a core D-glucosamine scaffold has allowed the evaluation of broad ranging structure activity relationships in ligand accelerated zincate additions to aldehydes, with variations in deltadeltaG+/+(R-S) of up to 5650 J mol(-1) that create opposing senses of asymmetric induction and that are consistent with models based on several ligand X-ray structures and molecular mechanics analysis. Factorial analysis of enantioselectivity using key dihedral angles and steric volume on N-2 also highlight the potential for the use of factorial design in ligand construction. |
| spellingShingle | Emmerson, D Villard, R Mugnaini, C Batsanov, A Howard, J Hems, W Tooze, R Davis, B Precise structure activity relationships in asymmetric catalysis using carbohydrate scaffolds to allow ready fine tuning: dialkylzinc-aldehyde additions. |
| title | Precise structure activity relationships in asymmetric catalysis using carbohydrate scaffolds to allow ready fine tuning: dialkylzinc-aldehyde additions. |
| title_full | Precise structure activity relationships in asymmetric catalysis using carbohydrate scaffolds to allow ready fine tuning: dialkylzinc-aldehyde additions. |
| title_fullStr | Precise structure activity relationships in asymmetric catalysis using carbohydrate scaffolds to allow ready fine tuning: dialkylzinc-aldehyde additions. |
| title_full_unstemmed | Precise structure activity relationships in asymmetric catalysis using carbohydrate scaffolds to allow ready fine tuning: dialkylzinc-aldehyde additions. |
| title_short | Precise structure activity relationships in asymmetric catalysis using carbohydrate scaffolds to allow ready fine tuning: dialkylzinc-aldehyde additions. |
| title_sort | precise structure activity relationships in asymmetric catalysis using carbohydrate scaffolds to allow ready fine tuning dialkylzinc aldehyde additions |
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