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Alkenes from β-lithiooxyphosphonium ylides generated by trapping α-lithiated terminal epoxides with triphenylphosphine.

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

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Publisher copy:
10.3762/bjoc.8.219

Authors


More by this author
Institution:
University of Oxford
Department:
Oxford, MPLS, Chemistry, Organic Chemistry
Persaud, RS More by this author
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:

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