Rongalite addition to dienones: diastereoselectivity in cyclic sulfone synthesis; stereochemical rationalization and prospects as a general conjugate nucleophile

• Melina Goga,
• Hao Zong,
• James Franco,
• Jazmine Prana,
• Rudolph Michel,
• Antonia Muro,
• Elana Rubin,
• Janet Brenya,
• Henk Eshuis and
• Magnus W. P. Bebbington

Beilstein J. Org. Chem. 2026, 22, 742–752, doi:10.3762/bjoc.22.56

• experimental and computational study of the diastereoselectivity of cyclic sulfone synthesis by reaction of Rongalite with doubly electrophilic dienones is presented. Computational methods, including density functional theory, conformational search methods, and internal reaction coordinate methods, have been

• used to rationalize the diastereoselectivity of the reaction by transition-state modeling, and showcases the conformational subtleties of sulfur-containing rings. Extension of the original reaction to double intermolecular additions is also demonstrated along with a comparative study of Rongalite with

• the reactivity of other readily available sulfinate nucleophiles using competition and exchange experiments. Keywords: diastereoselectivity; Rongalite; sulfones; Introduction Sulfonyl groups are widespread in licensed drugs [1]. New methods for the incorporation of sulfonyl groups into organic

Diversity-oriented synthesis of spirothiazolidinediones and their biological evaluation

• Sambasivarao Kotha,
• Gaddamedi Sreevani,
• Lilya U. Dzhemileva,
• Milyausha M. Yunusbaeva,
• Usein M. Dzhemilev and
• Vladimir A. D’yakonov

Beilstein J. Org. Chem. 2019, 15, 2774–2781, doi:10.3762/bjoc.15.269

• spirothiazolidinedione derivatives (Scheme 4). Further, the dibromo N-methyl derivative of thiazolidinedione 8b was converted to sultine 13 using rongalite and tetra-n-butylammonium bromide (TBAB) in DMF. Then, sultine 13 was treated with different dienophiles 14 in a DA fashion and linearly fused spirocyclic

β-Hydroxy sulfides and their syntheses

• Mokgethwa B. Marakalala,
• Edwin M. Mmutlane and
• Henok H. Kinfe

Beilstein J. Org. Chem. 2018, 14, 1668–1692, doi:10.3762/bjoc.14.143

• from the thiophenol to form β-peroxysulfide 84. Cleavage of the O–O bond of the peroxide followed by protonation liberates the desired β-hydroxy sulfide 81. This methodology is quite general considering the number of substituents used in both the styrenes and thiophenols. 3.2.4 Rongalite catalysis

• . Yadav et al. reported a very efficient one pot protocol of β-hydroxy sulfides synthesis from disulfides and styrenes in open air, at room temperature, using inexpensive Rongalite [sodium formaldehyde sulfoxylate (Na(HOCH2SO2)·2H2O)], as a promoter (Scheme 30) [67]. The protocol is compatible with

• disulfides and alkenes. tert-Butyl hydroperoxide-catalyzed hydroxysulfurization of alkenes. Proposed mechanism of the radical hydroxysulfurization. Rongalite-mediated synthesis of β-hydroxy sulfides from styrenes and disulfides. Proposed mechanism of Rongalite-mediated synthesis of β-hydroxy sulfides from

New metathesis catalyst bearing chromanyl moieties at the N-heterocyclic carbene ligand

• Agnieszka Hryniewicka,
• Szymon Suchodolski,
• Agnieszka Wojtkielewicz,
• Jacek W. Morzycki and
• Stanisław Witkowski

Beilstein J. Org. Chem. 2015, 11, 2795–2804, doi:10.3762/bjoc.11.300

• C14H19NNaO3: 272.1257, found: 272.1252. Literature mp 125–126 °C; IR, 1H NMR and 13C NMR data are compatible with the data in [39]. 2,2,5,7,8-Pentamethylchromanyl-6-amine (12) To the solution of rongalite (sodium hydroxymethylsulfinate dihydrate) (4.62 g, 5 equiv, 30 mmol) in a solution of 1 M NaOH (150 mL