- Abstract:
- 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.
- Publication status:
- Published
- Publisher copy:
- 10.3762/bjoc.8.219
-
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- Journal:
- Beilstein journal of organic chemistry
- Volume:
- 8
- Pages:
- 1896-1900
- Publication date:
- 2012
- DOI:
- EISSN:
-
1860-5397
- ISSN:
-
1860-5397
- URN:
-
uuid:6e248072-6d94-40bd-a0c6-8ae7a2f4953c
- Source identifiers:
-
365479
- Local pid:
- pubs:365479
- Language:
- English
- Keywords:
- Copyright date:
- 2012
Journal article
Alkenes from β-lithiooxyphosphonium ylides generated by trapping α-lithiated terminal epoxides with triphenylphosphine.
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