6533b86ffe1ef96bd12ce7a8

RESEARCH PRODUCT

2-Sulfoximidoyl Acetic Acids from Multicomponent Petasis Reactions and Their Use as Building Blocks in Syntheses of Sulfoximine Benzodiazepine Analogues.

Carsten BolmKari RissanenHeliana Michaela Núñez PonceKhai-nghi TruongRenè Hommelsheim

subject

BenzodiazepinePetasis reaction010405 organic chemistrymedicine.drug_classChemistryOrganic ChemistrymedicinePhysical and Theoretical Chemistry010402 general chemistry01 natural sciencesBiochemistryCombinatorial chemistry0104 chemical sciences

description

Upon application of a multicomponent Petasis reaction, a broad range of NH-sulfoximines and boronic acids react with glyoxalic acid to afford the corresponding 2-substituted acetic acids with N-bound sulfoximidoyl groups. The protocol features excellent yields under ambient, metal-free conditions and short reaction times. Furthermore, the applicability of 2-sulfoximidoyl acetic acids as building blocks for synthesizing sulfoximine-based benzodiazepine analogues was demonstrated.

10.1021/acs.orglett.1c00874https://pubmed.ncbi.nlm.nih.gov/33830781