Asymmetric sulfonylation with sulfur dioxide surrogates: a new access to enantiomerically enriched sulfones

Abstract

Enantiomerically enriched sulfones occupy a prominent position in pharmaceutical chemistry and synthetic chemistry. Comparing with conventional methods, direct asymmetric sulfonylation reaction with the fixation of sulfur dioxide represents an attractive...

Annulative Aminosulfonylation of Unactivated Alkenes for Accessing Pyrazolines via Multicomponent SO2 Insertion

“…On the other hand, the sulfonyl group is a valuable functional group in organic synthesis and has shown interesting application potential in drug design and synthesis . Therefore, numerous synthetic methods for accessing sulfonyl-containing compounds have been developed to date, , and of these, the vast majority of the developed approaches have focused on SO 2 insertion strategies. , For example, Wu and co-workers disclosed that arylsulfonyl radicals generated in situ through the combination of DABSO and aryldiazonium salts could serve as an efficient intermediate for arylsulfonylation . To continue our interest in heterocyclic synthesis, here, we report that aryl diazonium tetrafluoroborate and DABSO reacted with β,γ-unsaturated hydrazones to afford arylsulfonyl pyrazolins in the absence of any external oxidant or catalysts (Scheme c).…”

Access to chiral β-amino sulfones from acrylamides and sulfur dioxide by iron catalysis

“…However, this strategy has not yet to be reported in the asymmetric synthesis of chiral β-amino sulfones, signifying the need for further research in this field. Drawing from our ongoning research focus on the transformation of SO 2 , 13 and the lack of asymmetric sulfonation via sulfur dioxide insertion strategy, 14 we embark upon the development of the first asymmetric synthesis of chiral β-azide sulfones through alkene functionalization utilizing SO 2 insertion. Specifically, we aimed for the enantioselective coupling of α, β-unsaturated amides, cycloketoxime esters, 15 TMSN 3 , and gaseous SO 2 (from SOgen), 16 by exploiting abundant, highly accessible, and low-lost iron catalyst (Scheme 1c).…”

Multicomponent Reactions Based on SO2 Surrogates: Recent Advances

“…This superiority has significantly promoted the exploration of multicomponent sulfonylation reactions. [10a] In addition, some asymmetric MCRs have been investigated and succeeded in the synthesis of high value-added chiral sulfones, [12] although the complexity of multicomponent reaction systems and catalyst poisoning effect caused by SO 2 [13] make the enantioselective control challenging.…”