Synthesis and butyllithium-induced cyclisation of 2-benzyloxyphenylphosphonamidates giving 2,3-dihydrobenzo[d][1,3]oxaphospholes

R Alan Aitken; Khadija Ait Moulay; David Bradford Cordes; Ryan Inwood; Fraser G. Jamieson; Alexander J. B. Nelson; Aidan McKay

doi:10.3390/org5010002

Synthesis and butyllithium-induced cyclisation of 2-benzyloxyphenylphosphonamidates giving 2,3-dihydrobenzo[d][1,3]oxaphospholes

R Alan Aitken^*, Khadija Ait Moulay, David Bradford Cordes, Ryan Inwood, Fraser G. Jamieson, Alexander J. B. Nelson, Aidan McKay

^*Corresponding author for this work

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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.

Original language	English
Pages (from-to)	12-31
Number of pages	20
Journal	Organics
Volume	5
Issue number	1
DOIs	https://doi.org/10.3390/org5010002
Publication status	Published - 1 Feb 2024

Keywords

1,3-dihydrobenzo[d][1,3]oxaphosphole
1,3-benzoxaphosphole
Phosphonamidate
X-ray structure
Hydrogen bonding

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10.3390/org5010002Licence: CC BY

Aitken_2024_Organics_Synthesis_CCBY
Copyright © 2024 by the authors. Licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution (CC BY) license (https://creativecommons.org/licenses/by/4.0/).
Final published version, 1 MBLicence: CC BY

https://www.mdpi.com/2673-401X/5/1/2Licence: CC BY

CRITICAT CDT: Critical Resource Catalysis - CRITICAT
Smith, A. D. (PI), Nolan, S. P. (CoI) & Westwood, N. J. (CoI)
EPSRC
1/05/14 → 31/10/22
Project: Standard

Synthesis and Base-induced Cyclisation of 2-Benzyloxyphenylphosphonamidates giving 2,3-Dihydrobenzo[d][1,3]oxaphospholes (dataset)
Aitken, R. A. (Creator), Ait Moulay, K. (Creator), Cordes, D. B. (Creator), Inwood, R. (Creator), Jamieson, F. G. (Creator), Nelson, A. J. B. (Creator) & McKay, A. (Creator), University of St Andrews, 2 Feb 2024
DOI: 10.17630/d69e06d9-b2f1-4a61-9650-34068e4aa221
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title = "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.",

keywords = "1,3-dihydrobenzo[d][1,3]oxaphosphole, 1,3-benzoxaphosphole, Phosphonamidate, X-ray structure, Hydrogen bonding",

author = "Aitken, {R Alan} and {Ait Moulay}, Khadija and Cordes, {David Bradford} and Ryan Inwood and Jamieson, {Fraser G.} and Nelson, {Alexander J. B.} and Aidan McKay",

note = "Authors thank EPSRC (UK) and CRITICAT Centre for Doctoral Training for a studentship to R.A.I. (Grant EP/L016419/1).",

year = "2024",

month = feb,

day = "1",

doi = "10.3390/org5010002",

language = "English",

volume = "5",

pages = "12--31",

journal = "Organics",

issn = "2673-401X",

publisher = "MDPI",

number = "1",

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TY - JOUR

T1 - Synthesis and butyllithium-induced cyclisation of 2-benzyloxyphenylphosphonamidates giving 2,3-dihydrobenzo[d][1,3]oxaphospholes

AU - Aitken, R Alan

AU - Ait Moulay, Khadija

AU - Cordes, David Bradford

AU - Inwood, Ryan

AU - Jamieson, Fraser G.

AU - Nelson, Alexander J. B.

AU - McKay, Aidan

N1 - Authors thank EPSRC (UK) and CRITICAT Centre for Doctoral Training for a studentship to R.A.I. (Grant EP/L016419/1).

PY - 2024/2/1

Y1 - 2024/2/1

N2 - 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.

AB - 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.

KW - 1,3-dihydrobenzo[d][1,3]oxaphosphole

KW - 1,3-benzoxaphosphole

KW - Phosphonamidate

KW - X-ray structure

KW - Hydrogen bonding

U2 - 10.3390/org5010002

DO - 10.3390/org5010002

M3 - Article

SN - 2673-401X

VL - 5

SP - 12

EP - 31

JO - Organics

JF - Organics

IS - 1

ER -

Synthesis and butyllithium-induced cyclisation of 2-benzyloxyphenylphosphonamidates giving 2,3-dihydrobenzo[d][1,3]oxaphospholes

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Keywords

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CRITICAT CDT: Critical Resource Catalysis - CRITICAT

Datasets

Synthesis and Base-induced Cyclisation of 2-Benzyloxyphenylphosphonamidates giving 2,3-Dihydrobenzo[d][1,3]oxaphospholes (dataset)

Cite this