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Issue 32, 2018
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Phenolate-induced intramolecular ring-opening cyclization of N-tosylaziridines: access to functionalized benzoxacycles

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Abstract

Phenolate-induced, diastereo- and regioselective intramolecular exo-tet ring-opening cyclization of N-tosylaziridines has been achieved for the first time. The N-tosylaziridine substrates bearing a tethered (ortho-(tert-butyldimethylsiloxy))aryl substituent, prepared directly from the corresponding olefins under Sharpless aziridination conditions, furnished functionalized 2,3-dihydrobenzofuran, chroman, and 1-benzoxepane derivatives in excellent yields when treated with tetrabutylammonium fluoride (TBAF) at room temperature. Our ability to synthesize benzoxacycle-based N-tosyl-protected amino alcohols, that are otherwise difficult to obtain by traditional synthetic routes, has opened the door to diversify the chemistry of β-amino alcohols. We also succesfully performed the Baeyer–Villiger oxidation of a salicylaldehyde ether bearing a tethered N-tosylaziridine moiety with m-CPBA followed by tandem saponification and 6-exo-tet aziridine ring-opening cyclization, furnishing the corresponding trans-3,4-disubstituted-1,4-benzodioxane derivative. Overall, the study has unveiled a new entry to the synthesis of benzoxacycles and has also broadened the impact of aziridines as synthetic building blocks.

Graphical abstract: Phenolate-induced intramolecular ring-opening cyclization of N-tosylaziridines: access to functionalized benzoxacycles

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Publication details

The article was received on 16 May 2018, accepted on 24 Jul 2018 and first published on 25 Jul 2018


Article type: Paper
DOI: 10.1039/C8OB01143E
Citation: Org. Biomol. Chem., 2018,16, 5846-5858
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    Phenolate-induced intramolecular ring-opening cyclization of N-tosylaziridines: access to functionalized benzoxacycles

    R. Devi, J. Das, B. Sarma and S. K. Das, Org. Biomol. Chem., 2018, 16, 5846
    DOI: 10.1039/C8OB01143E

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