ASYMMETRIC-SYNTHESIS OF R-BETA-AMINO BUTANOIC ACID AND S-BETA-TYROSINE - HOMOCHIRAL LITHIUM AMIDE EQUIVALENTS FOR MICHAEL ADDITIONS TO ALPHA,BETA-UNSATURATED ESTERS
Michael addition of the lithium amide derived from R-N-(α-methylbenzyl)benzylamine to benzyl E-crotonate is highly stereoselective (95% d.e.) giving after debenzylation and crystallisation homochiral R-β-amino butanoic acid. A similar addition to methyl E-(p-benzyloxy)cinnamate is completely stereos...
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| Format: | Journal article |
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1991
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| _version_ | 1797062148702076928 |
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| author | Davies, S Ichihara, O |
| author_facet | Davies, S Ichihara, O |
| author_sort | Davies, S |
| collection | OXFORD |
| description | Michael addition of the lithium amide derived from R-N-(α-methylbenzyl)benzylamine to benzyl E-crotonate is highly stereoselective (95% d.e.) giving after debenzylation and crystallisation homochiral R-β-amino butanoic acid. A similar addition to methyl E-(p-benzyloxy)cinnamate is completely stereoselective giving after debenzylation and acid hydrolysis homochiral S-β-tyrosine as its HCl salt. © 1993. |
| first_indexed | 2024-03-06T20:41:26Z |
| format | Journal article |
| id | oxford-uuid:346bcda7-4229-4f95-84e6-b21d1f3ce1c4 |
| institution | University of Oxford |
| last_indexed | 2024-03-06T20:41:26Z |
| publishDate | 1991 |
| record_format | dspace |
| spelling | oxford-uuid:346bcda7-4229-4f95-84e6-b21d1f3ce1c42022-03-26T13:25:47ZASYMMETRIC-SYNTHESIS OF R-BETA-AMINO BUTANOIC ACID AND S-BETA-TYROSINE - HOMOCHIRAL LITHIUM AMIDE EQUIVALENTS FOR MICHAEL ADDITIONS TO ALPHA,BETA-UNSATURATED ESTERSJournal articlehttp://purl.org/coar/resource_type/c_dcae04bcuuid:346bcda7-4229-4f95-84e6-b21d1f3ce1c4Symplectic Elements at Oxford1991Davies, SIchihara, OMichael addition of the lithium amide derived from R-N-(α-methylbenzyl)benzylamine to benzyl E-crotonate is highly stereoselective (95% d.e.) giving after debenzylation and crystallisation homochiral R-β-amino butanoic acid. A similar addition to methyl E-(p-benzyloxy)cinnamate is completely stereoselective giving after debenzylation and acid hydrolysis homochiral S-β-tyrosine as its HCl salt. © 1993. |
| spellingShingle | Davies, S Ichihara, O ASYMMETRIC-SYNTHESIS OF R-BETA-AMINO BUTANOIC ACID AND S-BETA-TYROSINE - HOMOCHIRAL LITHIUM AMIDE EQUIVALENTS FOR MICHAEL ADDITIONS TO ALPHA,BETA-UNSATURATED ESTERS |
| title | ASYMMETRIC-SYNTHESIS OF R-BETA-AMINO BUTANOIC ACID AND S-BETA-TYROSINE - HOMOCHIRAL LITHIUM AMIDE EQUIVALENTS FOR MICHAEL ADDITIONS TO ALPHA,BETA-UNSATURATED ESTERS |
| title_full | ASYMMETRIC-SYNTHESIS OF R-BETA-AMINO BUTANOIC ACID AND S-BETA-TYROSINE - HOMOCHIRAL LITHIUM AMIDE EQUIVALENTS FOR MICHAEL ADDITIONS TO ALPHA,BETA-UNSATURATED ESTERS |
| title_fullStr | ASYMMETRIC-SYNTHESIS OF R-BETA-AMINO BUTANOIC ACID AND S-BETA-TYROSINE - HOMOCHIRAL LITHIUM AMIDE EQUIVALENTS FOR MICHAEL ADDITIONS TO ALPHA,BETA-UNSATURATED ESTERS |
| title_full_unstemmed | ASYMMETRIC-SYNTHESIS OF R-BETA-AMINO BUTANOIC ACID AND S-BETA-TYROSINE - HOMOCHIRAL LITHIUM AMIDE EQUIVALENTS FOR MICHAEL ADDITIONS TO ALPHA,BETA-UNSATURATED ESTERS |
| title_short | ASYMMETRIC-SYNTHESIS OF R-BETA-AMINO BUTANOIC ACID AND S-BETA-TYROSINE - HOMOCHIRAL LITHIUM AMIDE EQUIVALENTS FOR MICHAEL ADDITIONS TO ALPHA,BETA-UNSATURATED ESTERS |
| title_sort | asymmetric synthesis of r beta amino butanoic acid and s beta tyrosine homochiral lithium amide equivalents for michael additions to alpha beta unsaturated esters |
| work_keys_str_mv | AT daviess asymmetricsynthesisofrbetaaminobutanoicacidandsbetatyrosinehomochirallithiumamideequivalentsformichaeladditionstoalphabetaunsaturatedesters AT ichiharao asymmetricsynthesisofrbetaaminobutanoicacidandsbetatyrosinehomochirallithiumamideequivalentsformichaeladditionstoalphabetaunsaturatedesters |