Non Camphor Based Sultam Chiral Auxiliaries

Lee, Albert W. M.; Chan, Wing Hong; Zhang, Shu Jia; Zhang, Hong Kui

doi:10.2174/138527207779316435

Cited by 18 publications

(1 citation statement)

References 18 publications

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“…Some papers survey the literature data on more specific categories of sultams, i.e. non‐camphor based sultam chiral auxiliaries (2007), benzothiazines (2018), or bridged sultams with a bridgehead nitrogen atom (as a part of a more general review on bridged lactams) . A year ago, a critical review of pharmaceutical and medicinal applications of sulfur (VI)‐containing motifs has also been published (2019) …”

Section: Introductionmentioning

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: Introductionmentioning

confidence: 99%

Saturated Bicyclic Sultams

et al. 2020

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Asymmetric Synthesis of Five‐Membered Ring Heterocycles with More Than One Heteroatom

Kadouri‐Puchot

Agami

2009

Asymmetric Synthesis of Nitrogen Heterocycles

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Dual Role of Vinyl Sulfonamides as N‐Nucleophiles and Michael Acceptors in the Enantioselective Synthesis of Bicyclic δ‐Sultams

et al. 2018

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A new methodology for the synthesis of enantiomerically enriched bicyclic δ‐sultams is described, involving an initial organocatalytic intramolecular aza‐Michael reaction of vinyl sulfonamides bearing a conjugated ketone at a remote position. The resulting Michael adducts were then subjected to an intramolecular conjugate addition over the vinyl sulfone moiety, thus rendering the final bicyclic sultams containing two stereocenters. The key point of this strategy relies on the use of vinyl sulfonamides as both, nitrogen nucleophiles and Michael acceptors. The use of phosphazene‐derived bases avoided the racemization of the intermediate derivatives, rendering 6‐membered ring bicyclic δ‐sultams in enantiomerically enriched manner with a small erosion of enantiopurity. Anyway, after recrystallization, final sultams were obtained in almost enantiomerically pure form. Nevertheless, the enantioselective synthesis of either 5‐membered ring products or benzofused derivatives was found to be out of the scope of our strategy.magnified image

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Non Camphor Based Sultam Chiral Auxiliaries

Cited by 18 publications

References 18 publications

Saturated Bicyclic Sultams

Saturated Bicyclic Sultams

Asymmetric Synthesis of Five‐Membered Ring Heterocycles with More Than One Heteroatom

Dual Role of Vinyl Sulfonamides as N‐Nucleophiles and Michael Acceptors in the Enantioselective Synthesis of Bicyclic δ‐Sultams

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