Asymmetric synthesis of beta-amino-gamma-substituted-gamma-butyrolactones: double diastereoselective conjugate addition of homochiral lithium amides to homochiral alpha,beta-unsaturated esters.
Chiral alpha,beta-unsaturated esters, containing a single, gamma-stereogenic centre, show modest levels of substrate control upon conjugate addition of lithium dibenzylamide. Double diastereoselective conjugate additions of homochiral lithium N-benzyl-N-(alpha-methylbenzyl)amide to the homochiral al...
| Main Authors: | , , , , , , , , , , |
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| Format: | Journal article |
| Language: | English |
| Published: |
2007
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| _version_ | 1826300881916657664 |
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| author | Cailleau, T Cooke, J Davies, S Ling, K Naylor, A Nicholson, R Price, P Roberts, P Russell, A Smith, A Thomson, J |
| author_facet | Cailleau, T Cooke, J Davies, S Ling, K Naylor, A Nicholson, R Price, P Roberts, P Russell, A Smith, A Thomson, J |
| author_sort | Cailleau, T |
| collection | OXFORD |
| description | Chiral alpha,beta-unsaturated esters, containing a single, gamma-stereogenic centre, show modest levels of substrate control upon conjugate addition of lithium dibenzylamide. Double diastereoselective conjugate additions of homochiral lithium N-benzyl-N-(alpha-methylbenzyl)amide to the homochiral alpha,beta-unsaturated esters display "matching" and "mismatching" effects. In each case, however, these additions proceed under the dominant stereocontrol of the lithium amide to give the corresponding beta-amino esters in high de. A remarkable reversal in stereoselectivity is noted by changing the ester functionality to an oxazolidinone. Subsequent O-deprotection and cyclisation of the resultant beta-amino adducts gives access to the corresponding beta-amino-gamma-substituted-gamma-butyrolactones in good yield and high de. |
| first_indexed | 2024-03-07T05:23:53Z |
| format | Journal article |
| id | oxford-uuid:dfe2611e-fce1-4e64-a153-6096d67088ba |
| institution | University of Oxford |
| language | English |
| last_indexed | 2024-03-07T05:23:53Z |
| publishDate | 2007 |
| record_format | dspace |
| spelling | oxford-uuid:dfe2611e-fce1-4e64-a153-6096d67088ba2022-03-27T09:42:35ZAsymmetric synthesis of beta-amino-gamma-substituted-gamma-butyrolactones: double diastereoselective conjugate addition of homochiral lithium amides to homochiral alpha,beta-unsaturated esters.Journal articlehttp://purl.org/coar/resource_type/c_dcae04bcuuid:dfe2611e-fce1-4e64-a153-6096d67088baEnglishSymplectic Elements at Oxford2007Cailleau, TCooke, JDavies, SLing, KNaylor, ANicholson, RPrice, PRoberts, PRussell, ASmith, AThomson, JChiral alpha,beta-unsaturated esters, containing a single, gamma-stereogenic centre, show modest levels of substrate control upon conjugate addition of lithium dibenzylamide. Double diastereoselective conjugate additions of homochiral lithium N-benzyl-N-(alpha-methylbenzyl)amide to the homochiral alpha,beta-unsaturated esters display "matching" and "mismatching" effects. In each case, however, these additions proceed under the dominant stereocontrol of the lithium amide to give the corresponding beta-amino esters in high de. A remarkable reversal in stereoselectivity is noted by changing the ester functionality to an oxazolidinone. Subsequent O-deprotection and cyclisation of the resultant beta-amino adducts gives access to the corresponding beta-amino-gamma-substituted-gamma-butyrolactones in good yield and high de. |
| spellingShingle | Cailleau, T Cooke, J Davies, S Ling, K Naylor, A Nicholson, R Price, P Roberts, P Russell, A Smith, A Thomson, J Asymmetric synthesis of beta-amino-gamma-substituted-gamma-butyrolactones: double diastereoselective conjugate addition of homochiral lithium amides to homochiral alpha,beta-unsaturated esters. |
| title | Asymmetric synthesis of beta-amino-gamma-substituted-gamma-butyrolactones: double diastereoselective conjugate addition of homochiral lithium amides to homochiral alpha,beta-unsaturated esters. |
| title_full | Asymmetric synthesis of beta-amino-gamma-substituted-gamma-butyrolactones: double diastereoselective conjugate addition of homochiral lithium amides to homochiral alpha,beta-unsaturated esters. |
| title_fullStr | Asymmetric synthesis of beta-amino-gamma-substituted-gamma-butyrolactones: double diastereoselective conjugate addition of homochiral lithium amides to homochiral alpha,beta-unsaturated esters. |
| title_full_unstemmed | Asymmetric synthesis of beta-amino-gamma-substituted-gamma-butyrolactones: double diastereoselective conjugate addition of homochiral lithium amides to homochiral alpha,beta-unsaturated esters. |
| title_short | Asymmetric synthesis of beta-amino-gamma-substituted-gamma-butyrolactones: double diastereoselective conjugate addition of homochiral lithium amides to homochiral alpha,beta-unsaturated esters. |
| title_sort | asymmetric synthesis of beta amino gamma substituted gamma butyrolactones double diastereoselective conjugate addition of homochiral lithium amides to homochiral alpha beta unsaturated esters |
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