Regioselective <i>O</i>‑Sulfonylation of <i>N</i>,<i>N</i>‑Bis(2-hydroxyalkyl)tosylamides as a Synthetic Key Step to Enantiopure Morpholines

The synthesis of enantiopure 2,6-disubstituted morpholines was realized through sequential ring opening of two different optically pure oxiranes by a tosylamide, under solid–liquid phase-transfer catalysis (SL-PTC) conditions, mono-<i>O</i>-sulfonylation of the resulting tosylamido-2,2′-diol, and cyclization to the morpholine. The crucial step, the regioselective formation of the monosulfonate, was controlled by taking advantage of the different stereo, electronic, and coordination properties of the oxirane-derived side chains in the diol backbone. As an application of this protocol, a new morpholine-3-carboxamide was synthesized starting from threonine

Memory of Chirality Approach to the Enantiodivergent Synthesis of Chiral Benzo[<i>d</i>]sultams

The “memory of chirality” stereodivergent synthesis of polyfluorobenzo[<i>d</i>]sultams has been developed. The interest of this protocol resides in the possibility of using the chirality of a starting sulfonamide single enantiomer to synthesize the target sultams in both absolute configurations, by using different base systems, under homogeneous conditions

Memory of Chirality Approach to the Enantiodivergent Synthesis of Chiral Benzo[<i>d</i>]sultams

The “memory of chirality” stereodivergent synthesis of polyfluorobenzo[<i>d</i>]sultams has been developed. The interest of this protocol resides in the possibility of using the chirality of a starting sulfonamide single enantiomer to synthesize the target sultams in both absolute configurations, by using different base systems, under homogeneous conditions

Memory of Chirality Approach to the Enantiodivergent Synthesis of Chiral Benzo[<i>d</i>]sultams

The “memory of chirality” stereodivergent synthesis of polyfluorobenzo[<i>d</i>]sultams has been developed. The interest of this protocol resides in the possibility of using the chirality of a starting sulfonamide single enantiomer to synthesize the target sultams in both absolute configurations, by using different base systems, under homogeneous conditions

Memory of Chirality Approach to the Enantiodivergent Synthesis of Chiral Benzo[<i>d</i>]sultams

The “memory of chirality” stereodivergent synthesis of polyfluorobenzo[<i>d</i>]sultams has been developed. The interest of this protocol resides in the possibility of using the chirality of a starting sulfonamide single enantiomer to synthesize the target sultams in both absolute configurations, by using different base systems, under homogeneous conditions