Comprehensive study towards the desulfonylation/desulfinylation of cis-3-functionalized 3-phenylsulfonyl/sulfinyl-β-lactams to access novel cis-3-monosubstituted-β-lactams. Issue 33 (16th August 2018) - Kumari, Anu
Abstract: An inclusive study towards the stereospecific synthesis of novel cis -3-monosubstituted-β-lactams from cis -3-functionalized 3-phenylsulfonyl/sulfinyl-β-lactams is described. 3-Sulfinyl-β-lactams 5/5ʹ successfully furnished stereospecific cis -3-monosubstituted-β-lactams 6, however 3-sulfonyl-β-lactams 2 failed to give the desulfurized product 6ʹ . The final stereochemical and structural conformations of novel β-lactams were established by single crystal X-ray crystallographic study (5c ). The cis configuration of the β-lactams 5/5ʹ and 6 was assigned in relevance to E and C4-H and C3-H and C4-H respectively. Graphical abstract: Image 1 Highlights: Stereoselective synthesis of novel diastereomeric C -3 functionalized 3-phenylsulfinyl-β-lactams. Straightforward, efficient and mild route to perform C -3 functionalization through Michael addition. Stereochemistry at C -3 of 3-functionalized sulfinyl β-lactam 5c was established by X-ray structural analysis. Successfully achieved stereospecifically cis -3-monosubstituted-β-lactams via desulfinylation.