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

作者：Parisi Giovanna; Degennaro Leonardo; Carlucci Claudia; de Candia Modesto; Mastrorilli Piero; Roller Alexander; Holzer Wolfgang; Altomare Cosimo Damiano^*; Pace Vittorio^*; Luisi Renzo^*

来源：Organic and Biomolecular Chemistry, 2017, 12(23): 5000-5015.

DOI：10.1039/c7ob00846e

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 k'(w)) 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.

• 出版日期2017-6-21