Sulfonyl bis-N-oxazolidinone (SBO): A new versatile dielectrophile with sequential reactivity

Sulfahydantoins as Tripeptide Constraints: Synthesis and Structure of Chiral Substituted 3-Oxo-1,2,5-thiadiazolidine 1,1-Dioxides

“…malate, lactate, or glycolate) under Mitsunobu conditions surprisingly gave the O-alkylated compound B with the hydroxy ester having the same absolute configuration (Scheme 1). [9] This has been proven by X-ray analysis of the O-lactim ether and a mechanism has been proposed for the unexpected reaction. In contrast, the use of allylic alcohol under the same conditions gave the expected N-alkylated compounds (C) (no transposition was observed) in near quantitative yields.…”

“…observed with the O-alkylated lactim. [9] The change of con-AAs models for sulfahydantoin-constrained tripeptides, formation also affects the signals of the methylenic protons the N 5 -acyldipeptides 38Ϫ43 were prepared by treatment of on the N2 in compounds 40 and 41. Furthermore, the hythe corresponding dipeptides with acetic anhydride in the bridization of the N5 becomes sp 2 and the angle ω of the presence of triethylamine.…”

Simple and efficient synthesis of new chiral N,N′‐sulfonyl bis‐oxazolidin‐2‐ones

“…As revealed by X-Ray crystallographic analysis [16], each heterocyclic moiety and S O group shows selective antiperiplanar orientation, which enhances values of α D for the chiral C2-dimeric forms 2a-e. SBO could be considered as a rigid skeleton grafted with substituents allowing structural and stereochemical diversity.…”

“…Previously, Dewynter et al reported the synthesis of sulfonyl bis-oxazolidin-2-one 2 for development of soft crosslinking and reticulation reagent for bionucleophiles [16]. Lee et al described the synthesis of the first hydrosoluble C-2 symmetric bis(oxazolidinone) [17] 1 as a potential bifunctional chiral auxiliary via regioselective intramolecular cyclization of the bis(carbamate).…”

Crystal structure of 4-methyl-N-{(E)-methyl[(3aR,8aS)-2-oxo-3,3a,8,8a-tetrahydro-2H-indeno[1,2-d][1,3]oxazol-3-yl]-λ4-sulfanylidene}benzenesulfonamide

“…For the synthesis, see: Celentano & Colonna (1998); Silveira & Marino (2013). For sulfonyl oxazolidinone structures, see: Barbey et al (2012); Berredjem et al (2010); Bonnaud et al (1987); Dewynter et al (1997). For related vinyl sulfonamide chemistry, see: .…”