Doubly diastereoselective conjugate additions of the antipodes of lithium N-benzyl-N-(alpha-methylbenzyl)amide to enantiopure epsilon-O-protected alpha,beta-unsaturated esters derived from D-ribose
Enantiopure ε-O-silyloxy- and ε-O-benzyloxy-α,β-unsaturated esters derived from d-ribose, each containing a cis-dioxolane unit, display excellent (≥95:5 dr) levels of diastereofacial directing ability upon conjugate addition of achiral lithium N-benzyl-N-isopropylamide. In contrast to the correspond...
| Main Authors: | , , , , |
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| Format: | Journal article |
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2014
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| _version_ | 1797065629956571136 |
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| author | Davies, S Foster, E Lee, J Roberts, P Thomson, J |
| author_facet | Davies, S Foster, E Lee, J Roberts, P Thomson, J |
| author_sort | Davies, S |
| collection | OXFORD |
| description | Enantiopure ε-O-silyloxy- and ε-O-benzyloxy-α,β-unsaturated esters derived from d-ribose, each containing a cis-dioxolane unit, display excellent (≥95:5 dr) levels of diastereofacial directing ability upon conjugate addition of achiral lithium N-benzyl-N-isopropylamide. In contrast to the corresponding enantiopure ε-O-silyloxy-α,β-unsaturated ester derived from l-tartaric acid, which contains a trans-dioxolane unit, the conjugate additions of the antipodes of lithium N-benzyl-N-(α-methylbenzyl)amide to its cis-configured counterpart result in doubly diastereoselective 'matched' and 'mismatched' reaction pairings in which the inherent reagent control serves to augment or oppose, respectively, the established substrate diastereocontrol. © 2014 Elsevier Ltd. All rights reserved. |
| first_indexed | 2024-03-06T21:31:23Z |
| format | Journal article |
| id | oxford-uuid:44ca3481-5f46-4a96-9779-24e845607da7 |
| institution | University of Oxford |
| last_indexed | 2024-03-06T21:31:23Z |
| publishDate | 2014 |
| record_format | dspace |
| spelling | oxford-uuid:44ca3481-5f46-4a96-9779-24e845607da72022-03-26T15:03:48ZDoubly diastereoselective conjugate additions of the antipodes of lithium N-benzyl-N-(alpha-methylbenzyl)amide to enantiopure epsilon-O-protected alpha,beta-unsaturated esters derived from D-riboseJournal articlehttp://purl.org/coar/resource_type/c_dcae04bcuuid:44ca3481-5f46-4a96-9779-24e845607da7Symplectic Elements at Oxford2014Davies, SFoster, ELee, JRoberts, PThomson, JEnantiopure ε-O-silyloxy- and ε-O-benzyloxy-α,β-unsaturated esters derived from d-ribose, each containing a cis-dioxolane unit, display excellent (≥95:5 dr) levels of diastereofacial directing ability upon conjugate addition of achiral lithium N-benzyl-N-isopropylamide. In contrast to the corresponding enantiopure ε-O-silyloxy-α,β-unsaturated ester derived from l-tartaric acid, which contains a trans-dioxolane unit, the conjugate additions of the antipodes of lithium N-benzyl-N-(α-methylbenzyl)amide to its cis-configured counterpart result in doubly diastereoselective 'matched' and 'mismatched' reaction pairings in which the inherent reagent control serves to augment or oppose, respectively, the established substrate diastereocontrol. © 2014 Elsevier Ltd. All rights reserved. |
| spellingShingle | Davies, S Foster, E Lee, J Roberts, P Thomson, J Doubly diastereoselective conjugate additions of the antipodes of lithium N-benzyl-N-(alpha-methylbenzyl)amide to enantiopure epsilon-O-protected alpha,beta-unsaturated esters derived from D-ribose |
| title | Doubly diastereoselective conjugate additions of the antipodes of lithium N-benzyl-N-(alpha-methylbenzyl)amide to enantiopure epsilon-O-protected alpha,beta-unsaturated esters derived from D-ribose |
| title_full | Doubly diastereoselective conjugate additions of the antipodes of lithium N-benzyl-N-(alpha-methylbenzyl)amide to enantiopure epsilon-O-protected alpha,beta-unsaturated esters derived from D-ribose |
| title_fullStr | Doubly diastereoselective conjugate additions of the antipodes of lithium N-benzyl-N-(alpha-methylbenzyl)amide to enantiopure epsilon-O-protected alpha,beta-unsaturated esters derived from D-ribose |
| title_full_unstemmed | Doubly diastereoselective conjugate additions of the antipodes of lithium N-benzyl-N-(alpha-methylbenzyl)amide to enantiopure epsilon-O-protected alpha,beta-unsaturated esters derived from D-ribose |
| title_short | Doubly diastereoselective conjugate additions of the antipodes of lithium N-benzyl-N-(alpha-methylbenzyl)amide to enantiopure epsilon-O-protected alpha,beta-unsaturated esters derived from D-ribose |
| title_sort | doubly diastereoselective conjugate additions of the antipodes of lithium n benzyl n alpha methylbenzyl amide to enantiopure epsilon o protected alpha beta unsaturated esters derived from d ribose |
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