Synthesis and butyllithium-induced cyclisation of 2-benzyloxyphenylphosphonamidates giving 2,3-dihydrobenzo[d][1,3]oxaphospholes
Abstract
A series of fourteen O-ethyl-N-butylphenylphosphonamidates with benzyl ether substituents at the ortho position have been prepared and fully characterised. Upon treatment with n-butyllithium in THF at RT, these undergo cyclisation in eight cases to give the novel 2,3-dihydrobenzo[d][1,3]oxaphospholes in moderate to low yield as a single diastereomer for which the relative configuration has been determined by X-ray diffraction in one case.
Citation
Aitken , R A , Ait Moulay , K , Cordes , D B , Inwood , R , Jamieson , F G , Nelson , A J B & McKay , A 2024 , ' Synthesis and butyllithium-induced cyclisation of 2-benzyloxyphenylphosphonamidates giving 2,3-dihydrobenzo[ d ][1,3]oxaphospholes ' , Organics , vol. 5 , no. 1 , pp. 12-31 . https://doi.org/10.3390/org5010002
Publication
Organics
Status
Peer reviewed
ISSN
2673-401XType
Journal article
Description
Authors thank EPSRC (UK) and CRITICAT Centre for Doctoral Training for a studentship to R.A.I. (Grant EP/L016419/1).Collections
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