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)

• Record Type: Journal Article
• Authors: Kumari, Anu; Bari, S.S.; Modi, Garima; Berry, Shiwani; Khullar, Sadhika; Mandal, Sanjay K.; Bhalla, Aman
• Is Part Of: Tetrahedron. Volume 74:Issue 33(2018)
• Page Start: 4400
• Page End: 4408
• Publication Date: 2018-08-16
• Subjects: trans-3-Phenylsulfinyl-β-lactams -- C-3 functionalization -- Michael addition -- cis-β-Lactam adducts -- Desulfonylation/desulfinylation -- cis-3-Monosubstituted-β-lactams; Chemistry, Organic -- Periodicals; 547.005
• DOI: 10.1016/j.tet.2018.07.008
• Languages: English
• ISSNs: 0040-4020

Abstract

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.