Alkenes from β-lithiooxyphosphonium ylides generated by trapping α-lithiated terminal epoxides with triphenylphosphine.
Terminal epoxides undergo lithium 2,2,6,6-tetramethylpiperidide-induced α-lithiation and subsequent interception with Ph(3)P to provide a new and direct entry to β-lithiooxyphosphonium ylides. The intermediacy of such an ylide is demonstrated by representative alkene-forming reactions with chloromet...
| Main Authors: | , |
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| Format: | Journal article |
| Language: | English |
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2012
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| _version_ | 1797074523925774336 |
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| author | Hodgson, D Persaud, R |
| author_facet | Hodgson, D Persaud, R |
| author_sort | Hodgson, D |
| collection | OXFORD |
| description | Terminal epoxides undergo lithium 2,2,6,6-tetramethylpiperidide-induced α-lithiation and subsequent interception with Ph(3)P to provide a new and direct entry to β-lithiooxyphosphonium ylides. The intermediacy of such an ylide is demonstrated by representative alkene-forming reactions with chloromethyl pivalate, benzaldehyde and CD(3)OD, giving a Z-allylic pivalate, a conjugated E-allylic alcohol and a partially deuterated terminal alkene, respectively, in modest yields. |
| first_indexed | 2024-03-06T23:37:26Z |
| format | Journal article |
| id | oxford-uuid:6e248072-6d94-40bd-a0c6-8ae7a2f4953c |
| institution | University of Oxford |
| language | English |
| last_indexed | 2024-03-06T23:37:26Z |
| publishDate | 2012 |
| record_format | dspace |
| spelling | oxford-uuid:6e248072-6d94-40bd-a0c6-8ae7a2f4953c2022-03-26T19:22:23ZAlkenes from β-lithiooxyphosphonium ylides generated by trapping α-lithiated terminal epoxides with triphenylphosphine.Journal articlehttp://purl.org/coar/resource_type/c_dcae04bcuuid:6e248072-6d94-40bd-a0c6-8ae7a2f4953cEnglishSymplectic Elements at Oxford2012Hodgson, DPersaud, RTerminal epoxides undergo lithium 2,2,6,6-tetramethylpiperidide-induced α-lithiation and subsequent interception with Ph(3)P to provide a new and direct entry to β-lithiooxyphosphonium ylides. The intermediacy of such an ylide is demonstrated by representative alkene-forming reactions with chloromethyl pivalate, benzaldehyde and CD(3)OD, giving a Z-allylic pivalate, a conjugated E-allylic alcohol and a partially deuterated terminal alkene, respectively, in modest yields. |
| spellingShingle | Hodgson, D Persaud, R Alkenes from β-lithiooxyphosphonium ylides generated by trapping α-lithiated terminal epoxides with triphenylphosphine. |
| title | Alkenes from β-lithiooxyphosphonium ylides generated by trapping α-lithiated terminal epoxides with triphenylphosphine. |
| title_full | Alkenes from β-lithiooxyphosphonium ylides generated by trapping α-lithiated terminal epoxides with triphenylphosphine. |
| title_fullStr | Alkenes from β-lithiooxyphosphonium ylides generated by trapping α-lithiated terminal epoxides with triphenylphosphine. |
| title_full_unstemmed | Alkenes from β-lithiooxyphosphonium ylides generated by trapping α-lithiated terminal epoxides with triphenylphosphine. |
| title_short | Alkenes from β-lithiooxyphosphonium ylides generated by trapping α-lithiated terminal epoxides with triphenylphosphine. |
| title_sort | alkenes from β lithiooxyphosphonium ylides generated by trapping α lithiated terminal epoxides with triphenylphosphine |
| work_keys_str_mv | AT hodgsond alkenesfromblithiooxyphosphoniumylidesgeneratedbytrappingalithiatedterminalepoxideswithtriphenylphosphine AT persaudr alkenesfromblithiooxyphosphoniumylidesgeneratedbytrappingalithiatedterminalepoxideswithtriphenylphosphine |