Imperial College London
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Dr James A Bull

Faculty of Natural Sciences, Department of Chemistry

Reader in Synthetic Chemistry
 
 
 
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Contact

 

+44 (0)20 7594 5811j.bull Website

 
 
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Location

 

501bMolecular Sciences Research HubWhite City Campus

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Summary

 

Publications

Citation

BibTex format

@article{Rojas:2022:10.1021/acs.orglett.2c00568,
author = {Rojas, Munoz J and Torrisi, E and Dubois, M and Hossain, R and White, A and Zappia, G and Mousseau, J and Choi, C and Bull, J},
doi = {10.1021/acs.orglett.2c00568},
journal = {Organic Letters},
title = {Oxetan-3-ols as 1,2-bis-Electrophiles in a brønsted acid catalyzed synthesis of 1,4-Dioxanes},
url = {http://dx.doi.org/10.1021/acs.orglett.2c00568},
volume = {24},
year = {2022}
}
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RIS format (EndNote, RefMan)

TY  - JOUR
AB  - Annulations that combine di-acceptors with bis-nucleophiles are uncommon. Here, we report the synthesis of 1,4-dioxanes from 3-aryloxetan-3-ols, as 1,2-bis-electrophiles, and 1,2-diols. Brønsted acid Tf2NH catalyzes both the selec-tive activation of the oxetanol, to form an oxetane carbocation that reacts with the diol, and intramolecular ring-opening of the oxetane. High regio and diastereoselectivity is achieved with unsymmetrical diols. The substituted dioxanes and fused bicyclic products present interesting motifs for drug discovery and can be further functionalized.
AU  - Rojas,Munoz J
AU  - Torrisi,E
AU  - Dubois,M
AU  - Hossain,R
AU  - White,A
AU  - Zappia,G
AU  - Mousseau,J
AU  - Choi,C
AU  - Bull,J
DO  - 10.1021/acs.orglett.2c00568
PY  - 2022///
SN  - 1523-7052
TI  - Oxetan-3-ols as 1,2-bis-Electrophiles in a brønsted acid catalyzed synthesis of 1,4-Dioxanes
T2  - Organic Letters
UR  - http://dx.doi.org/10.1021/acs.orglett.2c00568
UR  - https://pubs.acs.org/doi/10.1021/acs.orglett.2c00568
UR  - http://hdl.handle.net/10044/1/96039
VL  - 24
ER  -
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