BIFUNCTIONAL CHIRAL AUXILIARIES-8 - UTILIZATION OF TARTARIC ACID-DERIVED AUXILIARIES IN ALDOL AND ALKYLATION REACTIONS
The boron enolates of three new homochiral C2 symmetric 1,3-diacylimidazolidin-2-ones prepared from natural tartaric acid undergo highly diastereoselective aldol and alkylation reactions. Cleavage of these diastereomerically pure, adducts gives homochiral (1R,2S)-1-phenyl-2-methylpropane-1,3-diol an...
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| 格式: | Journal article |
| 语言: | English |
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1994
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| _version_ | 1826292938544513024 |
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| author | Davies, S Evans, G Pearce, S |
| author_facet | Davies, S Evans, G Pearce, S |
| author_sort | Davies, S |
| collection | OXFORD |
| description | The boron enolates of three new homochiral C2 symmetric 1,3-diacylimidazolidin-2-ones prepared from natural tartaric acid undergo highly diastereoselective aldol and alkylation reactions. Cleavage of these diastereomerically pure, adducts gives homochiral (1R,2S)-1-phenyl-2-methylpropane-1,3-diol and (2R,3R)-3-hydroxy-3-phenyl-2-methylpropanoic acid and (2S)-3-phenyl-2-methylpropan-1-ol (>92% ee). One of these auxiliaries, 4,5-dimethylimidazolidin-2-one, has the lowest effective molecular weight of any previously reported chiral auxiliary. © 1994. |
| first_indexed | 2024-03-07T03:22:24Z |
| format | Journal article |
| id | oxford-uuid:b7de1cc3-8052-47ee-b61c-d15c2bd771d6 |
| institution | University of Oxford |
| language | English |
| last_indexed | 2024-03-07T03:22:24Z |
| publishDate | 1994 |
| record_format | dspace |
| spelling | oxford-uuid:b7de1cc3-8052-47ee-b61c-d15c2bd771d62022-03-27T04:51:52ZBIFUNCTIONAL CHIRAL AUXILIARIES-8 - UTILIZATION OF TARTARIC ACID-DERIVED AUXILIARIES IN ALDOL AND ALKYLATION REACTIONSJournal articlehttp://purl.org/coar/resource_type/c_dcae04bcuuid:b7de1cc3-8052-47ee-b61c-d15c2bd771d6EnglishSymplectic Elements at Oxford1994Davies, SEvans, GPearce, SThe boron enolates of three new homochiral C2 symmetric 1,3-diacylimidazolidin-2-ones prepared from natural tartaric acid undergo highly diastereoselective aldol and alkylation reactions. Cleavage of these diastereomerically pure, adducts gives homochiral (1R,2S)-1-phenyl-2-methylpropane-1,3-diol and (2R,3R)-3-hydroxy-3-phenyl-2-methylpropanoic acid and (2S)-3-phenyl-2-methylpropan-1-ol (>92% ee). One of these auxiliaries, 4,5-dimethylimidazolidin-2-one, has the lowest effective molecular weight of any previously reported chiral auxiliary. © 1994. |
| spellingShingle | Davies, S Evans, G Pearce, S BIFUNCTIONAL CHIRAL AUXILIARIES-8 - UTILIZATION OF TARTARIC ACID-DERIVED AUXILIARIES IN ALDOL AND ALKYLATION REACTIONS |
| title | BIFUNCTIONAL CHIRAL AUXILIARIES-8 - UTILIZATION OF TARTARIC ACID-DERIVED AUXILIARIES IN ALDOL AND ALKYLATION REACTIONS |
| title_full | BIFUNCTIONAL CHIRAL AUXILIARIES-8 - UTILIZATION OF TARTARIC ACID-DERIVED AUXILIARIES IN ALDOL AND ALKYLATION REACTIONS |
| title_fullStr | BIFUNCTIONAL CHIRAL AUXILIARIES-8 - UTILIZATION OF TARTARIC ACID-DERIVED AUXILIARIES IN ALDOL AND ALKYLATION REACTIONS |
| title_full_unstemmed | BIFUNCTIONAL CHIRAL AUXILIARIES-8 - UTILIZATION OF TARTARIC ACID-DERIVED AUXILIARIES IN ALDOL AND ALKYLATION REACTIONS |
| title_short | BIFUNCTIONAL CHIRAL AUXILIARIES-8 - UTILIZATION OF TARTARIC ACID-DERIVED AUXILIARIES IN ALDOL AND ALKYLATION REACTIONS |
| title_sort | bifunctional chiral auxiliaries 8 utilization of tartaric acid derived auxiliaries in aldol and alkylation reactions |
| work_keys_str_mv | AT daviess bifunctionalchiralauxiliaries8utilizationoftartaricacidderivedauxiliariesinaldolandalkylationreactions AT evansg bifunctionalchiralauxiliaries8utilizationoftartaricacidderivedauxiliariesinaldolandalkylationreactions AT pearces bifunctionalchiralauxiliaries8utilizationoftartaricacidderivedauxiliariesinaldolandalkylationreactions |