Direct Synthesis of Nitrones via Transition-Metal-Free Ring-Opening of N-Tosylaziridines with the Nitrogen Atom of Various (E)-Aldoximes and (E)-Ketoximes

Synthesis ◽  
2019 ◽  
Vol 51 (21) ◽  
pp. 4043-4057
Author(s):  
Xing Li ◽  
Wenjing Yan ◽  
Rui Zhang ◽  
Honghong Chang ◽  
Wenchao Gao ◽  
...  
Keyword(s):  
Nitrogen Atom ◽  
Transition Metal ◽  
Oxygen Atom ◽  
Ring Opening ◽  
Direct Synthesis ◽  
Reaction Conditions ◽  
Free Ring ◽  
Metal Free ◽  
Ring Opening Reaction ◽  
Ring Opening Reactions

The KOH-, K2CO3-, or Et3N-catalyzed ring-opening reaction of N-tosylaziridines using the nitrogen atom of a series of (E)-aldoximes and (E)-ketoximes as a nucleophilic atom instead of an oxygen atom was developed to construct various nitrones under mild reaction conditions. Diverse (E)-aldoximes and (E)-ketoximes were demonstrated to be compatible with this reaction and the products of O-ring-opening reactions were not detected for most examples.

scholarly journals Straightforward Strategies for the Preparation of NH-Sulfox­imines: A Serendipitous Story

Synlett ◽  
2017 ◽  
Vol 28 (19) ◽  
pp. 2525-2538 ◽  
Author(s):  
James Bull ◽  
Renzo Luisi ◽  
Leonardo Degennaro
Keyword(s):  
Transition Metal ◽  
Physicochemical Properties ◽  
Direct Synthesis ◽  
Transition Metal Catalysts ◽  
Hypervalent Iodine ◽  
Reaction Conditions ◽  
One Pot ◽  
Metal Free ◽  
Recent Developments ◽  
New Procedures

Sulfoximines are emerging as valuable new isosteres for use in medicinal chemistry, with the potential to modulate physicochemical properties. Recent developments in synthetic strategies have made the unprotected ‘free’ NH-sulfoximine group more readily available, facilitating further study. This account reviews approaches to NH-sulfoximines, with a focus on our contribution to the field. Starting from the development of catalytic strategies involving transition metals, more sustainable metal-free processes have been discovered. In particular, the use of hypervalent iodine reagents to mediate NH-transfer to sulfoxides is described, along with an assessment of the substrate scope. Furthermore, a one-pot strategy to convert sulfides directly into NH-sulfoximines is discussed, with N- and O-transfer occurring under the reaction conditions. Mechanistic evidence for the new procedures is included as well as relevant synthetic applications that further exemplify the potential of these approaches.1 Introduction2 Strategies to Form NH-Sulfoximines Involving Transition-Metal Catalysts3 Metal-Free Strategies to Prepare NH-Sulfoximines4 Mechanistic Evidence for the Direct Synthesis of NH-Sulfoximines from Sulfoxides and Sulfides5 Further Applications6 Conclusion

Transition-Metal-Free Ring-Opening Silylation of Indoles and Benzofurans with (Diphenyl-tert -butylsilyl)lithium

2017 ◽  
Vol 56 (44) ◽  
pp. 13872-13875 ◽  
Author(s):  
Pan Xu ◽  
Ernst-Ulrich Würthwein ◽  
Constantin G. Daniliuc ◽  
Armido Studer
Keyword(s):  
Transition Metal ◽  
Ring Opening ◽  
Free Ring ◽  
Metal Free

scholarly journals Mild and selective silicon-mediated access to enantioenriched 1,2-mercaptoamines and β-amino arylchalcogenides

2019 ◽  
Vol 43 (16) ◽  
pp. 6388-6393 ◽  
Author(s):  
Damiano Tanini ◽  
Cosimo Borgogni ◽  
Antonella Capperucci
Keyword(s):  
Ring Opening ◽  
Free Ring ◽  
Metal Free ◽  
Ring Opening Reactions

Metal-free ring opening reactions of activated and unactivated aziridines with different silyl chalcogenides are described.

Recent Advances in Transition Metal Catalyzed C-H Functionalization Reactions Involving Aza/Oxabicyclic Alkenes

Synthesis ◽  
2021 ◽  
Author(s):  
Masilamani Jeganmohan ◽  
Pinki Sihag
Keyword(s):  
Transition Metal ◽  
Metal Complexes ◽  
Transition Metal Complexes ◽  
Ring Opening ◽  
Bond Activation ◽  
Considerable Progress ◽  
Double Bonds ◽  
Facial Selectivity ◽  
Ring Opening Reactions ◽  
Metal Catalyzed

Bicyclic alkenes, including Oxa- and azabicyclic alkenes can be readily activated by using transition-metal complexes with facial selectivity, because of the intrinsic angle strain on carbon-carbon double bonds of these unsymmetrical bicyclic systems. During last decades considerable progress has been done in the area of ring-opening of bicyclic strained ring by employing the concept of C-H activation. This Review comprehensively compiles the various C-H bond activation assisted reactions of oxa- and azabicyclic alkenes, viz., ring-opening reactions, hydroarylation as well as annulation reactions.

scholarly journals Phosphetes via transition metal free ring closure – taking the proper turn at a thermodynamic crossing

2021 ◽  
Author(s):  
Rudolf Pietschnig ◽  
Fabian Roesler ◽  
Máté Kovács ◽  
Clemens Bruhn ◽  
Zsolt Kelemen
Keyword(s):  
Transition Metal ◽  
Ring Closure ◽  
Free Ring ◽  
Metal Free

scholarly journals Phosphetes via Transition Metal Free Ring Closure – Taking the Proper Turn at a Thermodynamic Crossing

2021 ◽  
Author(s):  
Fabian Roesler ◽  
Máté Kovács ◽  
Clemens Bruhn ◽  
Zsolt Kelemen ◽  
Rudolf Pietschnig
Keyword(s):  
Transition Metal ◽  
Ring Closure ◽  
Free Ring ◽  
Metal Free

Hydrolytic ring opening reactions of anhydrides for first row transition metal dicarboxylate complexes

Polyhedron ◽  
2007 ◽  
Vol 26 (15) ◽  
pp. 4518-4524 ◽  
Author(s):  
Abhilasha M. Baruah ◽  
Anirban Karmakar ◽  
Jubaraj B. Baruah
Keyword(s):  
Transition Metal ◽  
Ring Opening ◽  
Ring Opening Reactions
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