α-Functionalisation of Cyclic Sulfides Enabled by Lithiation Trapping.

Area of Science:

• Organic Chemistry
• Heterocyclic Chemistry
• Synthetic Methodology

Background:

• Cyclic sulfides are important structural motifs in various chemical compounds.
• Existing methods for synthesizing α-substituted cyclic sulfides are limited in scope and efficiency.

Purpose of the Study:

• To develop a general and straightforward procedure for the synthesis of α-substituted saturated sulfur heterocycles.
• To expand the accessibility of diverse cyclic sulfide derivatives through a novel synthetic route.

Main Methods:

• The study employed a lithiation-trapping strategy.
• Cyclic sulfides, including tetrahydrothiophene, tetrahydrothiopyran, and thiomorpholine, were subjected to lithiation.
• The resulting lithiated intermediates were trapped with a wide array of electrophiles.

Main Results:

• A general and straightforward procedure for lithiation-trapping of cyclic sulfides was successfully established.
• Over 50 diverse α-substituted saturated sulfur heterocycles were synthesized.
• The methodology demonstrated broad applicability with various electrophiles.

Conclusions:

• The developed methodology provides efficient access to α-substituted cyclic sulfides.
• This new synthetic route overcomes limitations of current methods for preparing these valuable heterocyclic compounds.