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Issue 23, 2017
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A greener and efficient access to substituted four- and six-membered sulfur-bearing heterocycles

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Abstract

The regioselective functionalization of four- and six-membered cyclic sulfones was investigated using a lithiation/electrophile trapping strategy. The protocol features an interesting eco-compatibility profile because of the use of 2-MeTHF as a solvent (more eco-friendly than other organic solvents) and n-hexyllithium as a lithiating agent safer than other alkyllithium compounds. Several derivatives were prepared with different stereochemistry and substitution patterns. A number of selected derivatives, spanning a range of 5 log P units, were characterized for their lipophilicity through RP-HPLC. A good linear correlation, with a slope close to 1.0, was observed between the experimentally determined RP-HPLC lipophilicity parameters (log kw) and calculated log P (clog P) values, whereas a systematic difference in absolute values between the chromatographic parameters and in silico lipophilicity descriptors can be attributed mainly to silanophilic interactions between the H-bond acceptor SO2 group and free silanol groups on silica-based C18 columns, which results in increased retention times.

Graphical abstract: A greener and efficient access to substituted four- and six-membered sulfur-bearing heterocycles

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Publication details

The article was received on 05 Apr 2017, accepted on 16 May 2017 and first published on 18 May 2017


Article type: Paper
DOI: 10.1039/C7OB00846E
Citation: Org. Biomol. Chem., 2017,15, 5000-5015
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    A greener and efficient access to substituted four- and six-membered sulfur-bearing heterocycles

    G. Parisi, L. Degennaro, C. Carlucci, M. de Candia, P. Mastrorilli, A. Roller, W. Holzer, C. D. Altomare, V. Pace and R. Luisi, Org. Biomol. Chem., 2017, 15, 5000
    DOI: 10.1039/C7OB00846E

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