Synthesis and C-alkylation of hindered aldehyde enamines.
A new reactivity mode of hindered lithium amides with terminal epoxides is described whereby aldehyde enamines are produced via a previously unrecognized reaction pathway. Some of these aldehyde enamines display unprecedented C-alkylation reactivity toward unactivated primary and secondary alkyl hal...
| Main Authors: | , , , , , , |
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| Format: | Journal article |
| Language: | English |
| Published: |
2009
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| _version_ | 1797070827613585408 |
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| author | Hodgson, D Bray, C Kindon, N Reynolds, N Coote, S Um, J Houk, K |
| author_facet | Hodgson, D Bray, C Kindon, N Reynolds, N Coote, S Um, J Houk, K |
| author_sort | Hodgson, D |
| collection | OXFORD |
| description | A new reactivity mode of hindered lithium amides with terminal epoxides is described whereby aldehyde enamines are produced via a previously unrecognized reaction pathway. Some of these aldehyde enamines display unprecedented C-alkylation reactivity toward unactivated primary and secondary alkyl halides. For comparison, the reactivity of aldehyde enamines synthesized via a traditional condensation method was examined. C- rather than N-alkylation was the dominant reaction pathway found with a range of electrophiles, making this route to alpha-alkylated aldehydes more synthetically useful than previously reported. |
| first_indexed | 2024-03-06T22:44:34Z |
| format | Journal article |
| id | oxford-uuid:5cb7f42d-4d0b-4b35-8ec8-85d7ad8e53a8 |
| institution | University of Oxford |
| language | English |
| last_indexed | 2024-03-06T22:44:34Z |
| publishDate | 2009 |
| record_format | dspace |
| spelling | oxford-uuid:5cb7f42d-4d0b-4b35-8ec8-85d7ad8e53a82022-03-26T17:30:01ZSynthesis and C-alkylation of hindered aldehyde enamines.Journal articlehttp://purl.org/coar/resource_type/c_dcae04bcuuid:5cb7f42d-4d0b-4b35-8ec8-85d7ad8e53a8EnglishSymplectic Elements at Oxford2009Hodgson, DBray, CKindon, NReynolds, NCoote, SUm, JHouk, KA new reactivity mode of hindered lithium amides with terminal epoxides is described whereby aldehyde enamines are produced via a previously unrecognized reaction pathway. Some of these aldehyde enamines display unprecedented C-alkylation reactivity toward unactivated primary and secondary alkyl halides. For comparison, the reactivity of aldehyde enamines synthesized via a traditional condensation method was examined. C- rather than N-alkylation was the dominant reaction pathway found with a range of electrophiles, making this route to alpha-alkylated aldehydes more synthetically useful than previously reported. |
| spellingShingle | Hodgson, D Bray, C Kindon, N Reynolds, N Coote, S Um, J Houk, K Synthesis and C-alkylation of hindered aldehyde enamines. |
| title | Synthesis and C-alkylation of hindered aldehyde enamines. |
| title_full | Synthesis and C-alkylation of hindered aldehyde enamines. |
| title_fullStr | Synthesis and C-alkylation of hindered aldehyde enamines. |
| title_full_unstemmed | Synthesis and C-alkylation of hindered aldehyde enamines. |
| title_short | Synthesis and C-alkylation of hindered aldehyde enamines. |
| title_sort | synthesis and c alkylation of hindered aldehyde enamines |
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