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 Ph3P 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 chloromethy...
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Beilstein-Institut
2012-11-01
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| Series: | Beilstein Journal of Organic Chemistry |
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| Online Access: | https://doi.org/10.3762/bjoc.8.219 |
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doaj-fcc463b589274b27b9d178f80f4af83b2021-02-02T08:46:32ZengBeilstein-InstitutBeilstein Journal of Organic Chemistry1860-53972012-11-01811896190010.3762/bjoc.8.2191860-5397-8-219Alkenes from β-lithiooxyphosphonium ylides generated by trapping α-lithiated terminal epoxides with triphenylphosphineDavid. M. Hodgson0Rosanne S. D. Persaud1Department of Chemistry, Chemistry Research Laboratory, University of Oxford, Mansfield Road, Oxford, OX1 3TA, UKDepartment of Chemistry, Chemistry Research Laboratory, University of Oxford, Mansfield Road, Oxford, OX1 3TA, UKTerminal epoxides undergo lithium 2,2,6,6-tetramethylpiperidide-induced α-lithiation and subsequent interception with Ph3P 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 CD3OD, giving a Z-allylic pivalate, a conjugated E-allylic alcohol and a partially deuterated terminal alkene, respectively, in modest yields.https://doi.org/10.3762/bjoc.8.219alkenesepoxideslithiationsynthetic methodsylide |
| collection |
DOAJ |
| language |
English |
| format |
Article |
| sources |
DOAJ |
| author |
David. M. Hodgson Rosanne S. D. Persaud |
| spellingShingle |
David. M. Hodgson Rosanne S. D. Persaud Alkenes from β-lithiooxyphosphonium ylides generated by trapping α-lithiated terminal epoxides with triphenylphosphine Beilstein Journal of Organic Chemistry alkenes epoxides lithiation synthetic methods ylide |
| author_facet |
David. M. Hodgson Rosanne S. D. Persaud |
| author_sort |
David. M. Hodgson |
| title |
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_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_sort |
alkenes from β-lithiooxyphosphonium ylides generated by trapping α-lithiated terminal epoxides with triphenylphosphine |
| publisher |
Beilstein-Institut |
| series |
Beilstein Journal of Organic Chemistry |
| issn |
1860-5397 |
| publishDate |
2012-11-01 |
| description |
Terminal epoxides undergo lithium 2,2,6,6-tetramethylpiperidide-induced α-lithiation and subsequent interception with Ph3P 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 CD3OD, giving a Z-allylic pivalate, a conjugated E-allylic alcohol and a partially deuterated terminal alkene, respectively, in modest yields. |
| topic |
alkenes epoxides lithiation synthetic methods ylide |
| url |
https://doi.org/10.3762/bjoc.8.219 |
| work_keys_str_mv |
AT davidmhodgson alkenesfromblithiooxyphosphoniumylidesgeneratedbytrappingalithiatedterminalepoxideswithtriphenylphosphine AT rosannesdpersaud alkenesfromblithiooxyphosphoniumylidesgeneratedbytrappingalithiatedterminalepoxideswithtriphenylphosphine |
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1724296531690913792 |