ASYMMETRIC-SYNTHESIS OF (1R,8S)-1-HYDROXYPYRROLIZIDIN-3-ONES AND (1S,8S)-1-HYDROXYPYRROLIZIDIN-3-ONES VIA THE ALDOL REACTION BETWEEN N-BOC-(S)-PROLINAL AND CHIRAL ACETATE ENOLATE EQUIVALENTS DERIVED FROM (S)-[(ETA-5-C5H5)FE(CO)(PPH3)COCH3] AND (R)-[(ETA-5-C5H5)FE(CO)(PPH3)COCH3]
Syntheses of both title compounds have been achieved with excellent stereocontrol using chiral acetate enolate equivalents derived from the iron acetyl complex [(η5-C5H5)Fe(CO)(PPh3)COCH3]. The different diastereoselectivities in the two syntheses are rationalised in terms of the concept of double a...
| Auteurs principaux: | , , |
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| Format: | Journal article |
| Langue: | English |
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1992
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| _version_ | 1826301774157316096 |
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| author | Beckett, R Davies, S Mortlock, A |
| author_facet | Beckett, R Davies, S Mortlock, A |
| author_sort | Beckett, R |
| collection | OXFORD |
| description | Syntheses of both title compounds have been achieved with excellent stereocontrol using chiral acetate enolate equivalents derived from the iron acetyl complex [(η5-C5H5)Fe(CO)(PPh3)COCH3]. The different diastereoselectivities in the two syntheses are rationalised in terms of the concept of double asymmetric induction and the transition state models for the aldol reactions of such enolates are discussed. © 1993. |
| first_indexed | 2024-03-07T05:37:27Z |
| format | Journal article |
| id | oxford-uuid:e466f0cc-a92e-4373-9901-42985310f9d1 |
| institution | University of Oxford |
| language | English |
| last_indexed | 2024-03-07T05:37:27Z |
| publishDate | 1992 |
| record_format | dspace |
| spelling | oxford-uuid:e466f0cc-a92e-4373-9901-42985310f9d12022-03-27T10:16:17ZASYMMETRIC-SYNTHESIS OF (1R,8S)-1-HYDROXYPYRROLIZIDIN-3-ONES AND (1S,8S)-1-HYDROXYPYRROLIZIDIN-3-ONES VIA THE ALDOL REACTION BETWEEN N-BOC-(S)-PROLINAL AND CHIRAL ACETATE ENOLATE EQUIVALENTS DERIVED FROM (S)-[(ETA-5-C5H5)FE(CO)(PPH3)COCH3] AND (R)-[(ETA-5-C5H5)FE(CO)(PPH3)COCH3]Journal articlehttp://purl.org/coar/resource_type/c_dcae04bcuuid:e466f0cc-a92e-4373-9901-42985310f9d1EnglishSymplectic Elements at Oxford1992Beckett, RDavies, SMortlock, ASyntheses of both title compounds have been achieved with excellent stereocontrol using chiral acetate enolate equivalents derived from the iron acetyl complex [(η5-C5H5)Fe(CO)(PPh3)COCH3]. The different diastereoselectivities in the two syntheses are rationalised in terms of the concept of double asymmetric induction and the transition state models for the aldol reactions of such enolates are discussed. © 1993. |
| spellingShingle | Beckett, R Davies, S Mortlock, A ASYMMETRIC-SYNTHESIS OF (1R,8S)-1-HYDROXYPYRROLIZIDIN-3-ONES AND (1S,8S)-1-HYDROXYPYRROLIZIDIN-3-ONES VIA THE ALDOL REACTION BETWEEN N-BOC-(S)-PROLINAL AND CHIRAL ACETATE ENOLATE EQUIVALENTS DERIVED FROM (S)-[(ETA-5-C5H5)FE(CO)(PPH3)COCH3] AND (R)-[(ETA-5-C5H5)FE(CO)(PPH3)COCH3] |
| title | ASYMMETRIC-SYNTHESIS OF (1R,8S)-1-HYDROXYPYRROLIZIDIN-3-ONES AND (1S,8S)-1-HYDROXYPYRROLIZIDIN-3-ONES VIA THE ALDOL REACTION BETWEEN N-BOC-(S)-PROLINAL AND CHIRAL ACETATE ENOLATE EQUIVALENTS DERIVED FROM (S)-[(ETA-5-C5H5)FE(CO)(PPH3)COCH3] AND (R)-[(ETA-5-C5H5)FE(CO)(PPH3)COCH3] |
| title_full | ASYMMETRIC-SYNTHESIS OF (1R,8S)-1-HYDROXYPYRROLIZIDIN-3-ONES AND (1S,8S)-1-HYDROXYPYRROLIZIDIN-3-ONES VIA THE ALDOL REACTION BETWEEN N-BOC-(S)-PROLINAL AND CHIRAL ACETATE ENOLATE EQUIVALENTS DERIVED FROM (S)-[(ETA-5-C5H5)FE(CO)(PPH3)COCH3] AND (R)-[(ETA-5-C5H5)FE(CO)(PPH3)COCH3] |
| title_fullStr | ASYMMETRIC-SYNTHESIS OF (1R,8S)-1-HYDROXYPYRROLIZIDIN-3-ONES AND (1S,8S)-1-HYDROXYPYRROLIZIDIN-3-ONES VIA THE ALDOL REACTION BETWEEN N-BOC-(S)-PROLINAL AND CHIRAL ACETATE ENOLATE EQUIVALENTS DERIVED FROM (S)-[(ETA-5-C5H5)FE(CO)(PPH3)COCH3] AND (R)-[(ETA-5-C5H5)FE(CO)(PPH3)COCH3] |
| title_full_unstemmed | ASYMMETRIC-SYNTHESIS OF (1R,8S)-1-HYDROXYPYRROLIZIDIN-3-ONES AND (1S,8S)-1-HYDROXYPYRROLIZIDIN-3-ONES VIA THE ALDOL REACTION BETWEEN N-BOC-(S)-PROLINAL AND CHIRAL ACETATE ENOLATE EQUIVALENTS DERIVED FROM (S)-[(ETA-5-C5H5)FE(CO)(PPH3)COCH3] AND (R)-[(ETA-5-C5H5)FE(CO)(PPH3)COCH3] |
| title_short | ASYMMETRIC-SYNTHESIS OF (1R,8S)-1-HYDROXYPYRROLIZIDIN-3-ONES AND (1S,8S)-1-HYDROXYPYRROLIZIDIN-3-ONES VIA THE ALDOL REACTION BETWEEN N-BOC-(S)-PROLINAL AND CHIRAL ACETATE ENOLATE EQUIVALENTS DERIVED FROM (S)-[(ETA-5-C5H5)FE(CO)(PPH3)COCH3] AND (R)-[(ETA-5-C5H5)FE(CO)(PPH3)COCH3] |
| title_sort | asymmetric synthesis of 1r 8s 1 hydroxypyrrolizidin 3 ones and 1s 8s 1 hydroxypyrrolizidin 3 ones via the aldol reaction between n boc s prolinal and chiral acetate enolate equivalents derived from s eta 5 c5h5 fe co pph3 coch3 and r eta 5 c5h5 fe co pph3 coch3 |
| work_keys_str_mv | AT beckettr asymmetricsynthesisof1r8s1hydroxypyrrolizidin3onesand1s8s1hydroxypyrrolizidin3onesviathealdolreactionbetweennbocsprolinalandchiralacetateenolateequivalentsderivedfromseta5c5h5fecopph3coch3andreta5c5h5fecopph3coch3 AT daviess asymmetricsynthesisof1r8s1hydroxypyrrolizidin3onesand1s8s1hydroxypyrrolizidin3onesviathealdolreactionbetweennbocsprolinalandchiralacetateenolateequivalentsderivedfromseta5c5h5fecopph3coch3andreta5c5h5fecopph3coch3 AT mortlocka asymmetricsynthesisof1r8s1hydroxypyrrolizidin3onesand1s8s1hydroxypyrrolizidin3onesviathealdolreactionbetweennbocsprolinalandchiralacetateenolateequivalentsderivedfromseta5c5h5fecopph3coch3andreta5c5h5fecopph3coch3 |