Synthese bicyclischer β‐Sultame

Cavagna, Friedrich; Koller, Wolfgang; Linkies, Adolf; Rehling, H.; Reuschling, D.

doi:10.1002/ange.19820940721

Cited by 15 publications

(2 citation statements)

References 3 publications

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“…[35,36] Several variations of this synthetic scheme were described in the literature. [37] The strategy was also applied for the synthesis of other bicyclic β-sultams 18/19, [38] 20, [39] and 21. [40] Scheme 8.…”

Section: Fused β-Sultamsmentioning

confidence: 99%

Saturated Bicyclic Sultams

et al. 2020

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Saturated bicyclic sultams represent a promising class of sp 3-rich three-dimensional scaffolds of outmost importance to organic and medicinal chemistry. In this review with 99 references, synthesis, properties, and applications of these compounds are surveyed. The literature data are categorized according to the structural types (i.e. fused, bridged, and spirocyclic compounds), as well as homologous series

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Section: Fused β-Sultamsmentioning

confidence: 99%

Saturated Bicyclic Sultams

et al. 2020

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“…Recently, β-sultams have received much attention in both synthetic and medicinal chemistry [ 1 , 2 , 3 , 4 , 5 , 6 , 7 , 8 ], mainly because of their outstanding biological activities as, for example, antibiotics and enzyme inhibitors [ 9 , 10 , 11 , 12 , 13 ]. As a result, many synthetic methods to β-sultams have been developed [ 14 , 15 , 16 , 17 ].…”

Section: Introductionmentioning

confidence: 99%

Ortho-Nitro Effect on the Diastereoselective Control in Sulfa-Staudinger and Staudinger Cycloadditions

Yang

Abdellaoui

et al. 2017

Molecules

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The ortho-nitro effect was discovered in sulfa-Staudinger cycloadditions of ethoxycarbonylsulfene with linear imines. When an ortho-nitro group is present at the C-aryl substituents of linear imines, the sulfa-Staudinger cycloadditions deliver cis-β-sultams in considerable amounts, together with the predominant trans-β-sultams. In other cases, the above sulfa-Staudinger cycloadditions give rise to trans-β-sultams exclusively. Further mechanistic rationalization discloses that the ortho-nitro effect is attributed to its strong electron-withdrawing inductive effect. Similarly, the ortho-nitro effect also exists in Staudinger cycloadditions of ethoxycarbonyl ketene with the imines. The current research provides further insights into the diastereoselective control in sulfa-Staudinger and Staudinger cycloadditions.

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