Generation and [2 + 2] Cycloadditions of Thio‐Substituted Ketenes:
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            ‐1‐(4‐Methoxyphenyl)‐4‐Phenyl‐3‐(Phenylthio)Azetidin‐2‐One

Danheiser, Rick; Okamoto, Iwao; Lawlor, Michael D.; Lee, Thomas W.

doi:10.1002/0471264180.os080.18

Cited by 10 publications

(6 citation statements)

References 9 publications

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“…Another mesoionic compound, although obtained with a different approach, found application in the synthesis of C-3 spirofused β-lactams . The catalysis of Rh complex is also effective in promoting a thia-Wolff rearrangement, transforming α-diazo thiol esters, such as 325 , into thiosubstituted ketenes . However, the same reaction can be performed without the use of the catalyst, increasing the temperature as shown in the next example for the diastereoselective preparation of 327 (Scheme )…”

Section: Azetidin-2-onesmentioning

confidence: 99%

Novel Syntheses of Azetidines and Azetidinones

2008

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Primary amines reacted upon 4,6-ditosylates of glucopyranosides 47 to give compounds 48a,c, with an azetidine ring formed between C4 and C6 of the pyranose ring, in good yields. Interestingly, corresponding mannopyranosides led to the uncyclized 4,6-diamino-4,6-dideoxy compounds (Scheme 13). 11f An azetidine isostere 52 of the oxetane-type taxane 1-deoxy-2-debenzoyloxy-4-deacetylbaccatin VI was synthesized starting from the alkaloid 2′-deacetoxyaustrospicatine 49 (Scheme 14). 10i Scheme

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Section: Azetidin-2-onesmentioning

confidence: 99%

Novel Syntheses of Azetidines and Azetidinones

2008

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“…Chlorosulfoxide 2 was prepared according to the method of Blakemore and co-workers . Imines 3 – 5 were prepared according to the procedure of Danheiser and co-workers . β-Chloroamines ( 6 – 8 ) were prepared by a modified version of the method of Satoh and co-workers …”

Section: Methodsmentioning

confidence: 99%

“…13b Imines 3−5 were prepared according to the procedure of Danheiser and co-workers. 34 β-Chloroamines (6− 8) were prepared by a modified version of the method of Satoh and co-workers. 35 Synthesis of Sulfinyl Aziridines 9−11.…”

Section: ■ Experimental Sectionmentioning

confidence: 99%

Palladium-Catalyzed Cross-Coupling of Aziridinylmetal Species, Generated by Sulfinyl–Magnesium Exchange, with Aryl Bromides: Reaction Optimization, Scope, and Kinetic Investigations

et al. 2013

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A series of novel, highly substituted N-PMP aziridines have been accessed in high yields by palladium-catalyzed cross-coupling of intact aziridines. The cross-coupling employed aryl bromides and tertiary organometallic aziridines, generated from sulfinylaziridines by sulfinyl-magnesium exchange and transmetalation to the aziridinylzinc with zinc chloride. A wide range of electron-rich and electron-poor aryl bromides were utilized to afford the functionalized aziridine products as single diastereoisomers with retention of configuration at the reacting center. Assessment of the reaction kinetics showed zero-order in both the aziridine species and the aryl bromide. This indicated that the rate-determining step was reductive elimination from the palladium(II) species bearing both the aziridine and aryl groups to form the hindered C-C bond. The intermediate aziridinylzinc species underwent a progressive, background degradation that led to a plateau in yield and afforded reduced yields in substrates with ortho-substituted aryl groups, which are less reactive due to the additional steric demands.

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“…Synthesis of Aldimines. 33 To a solution of substituted benzaldehyde (5 mmol) in dichloromethane (5 mL) were slowly added aniline (6 mmol). After 30 min, anhydrous magnesium sulfate (0.75 g) is added in one portion.…”

Section: ■ Experimental Sectionmentioning

confidence: 99%

Visible-Light Photocatalytic Synthesis of Amines from Imines via Transfer Hydrogenation Using Quantum Dots as Catalysts

Yang

Wang

et al. 2018

J. Org. Chem.

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CdSe/CdS core/shell quantum dots (QDs) can be used as stable and highly active photoredox catalysts for efficient transfer hydrogenation of imines to amines with thiophenol as a hydrogen atom donor. This reaction proceeds via a proton-coupled electron transfer (PCET) from the QDs conduction band to the protonated imine followed by hydrogen atom transfer from the thiophenol to the α-aminoalkyl radical. This precious metal free transformation is easy to scale up and can be carried out by a one-pot protocol directly from aldehyde, amine, and thiophenol. Additional advantageous features of this protocol include a wide substrate scope, high yield of the amine products, extremely low catalyst loading (0.001 mol %), high turnover number (10), and the mild reaction conditions of using visible light or sun light at room temperature in neutral media.

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Generation and [2 + 2] Cycloadditions of Thio‐Substituted Ketenes: trans ‐1‐(4‐Methoxyphenyl)‐4‐Phenyl‐3‐(Phenylthio)Azetidin‐2‐One

Abstract: N‐Benzylidene‐p‐anisidine Trans‐1‐(4‐Methoxyphenyl)‐4‐phenyl‐3‐(phenylthio)azetidin‐2‐one S‐Phenyldiazothioacetate Hexamethyldisilazane Butyllithium 2,2,2‐Trifluoroethyl trifluoroacetate

Cited by 10 publications

References 9 publications

Novel Syntheses of Azetidines and Azetidinones

Novel Syntheses of Azetidines and Azetidinones

Palladium-Catalyzed Cross-Coupling of Aziridinylmetal Species, Generated by Sulfinyl–Magnesium Exchange, with Aryl Bromides: Reaction Optimization, Scope, and Kinetic Investigations

Visible-Light Photocatalytic Synthesis of Amines from Imines via Transfer Hydrogenation Using Quantum Dots as Catalysts

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