117901-60-7

Upstream product

• 109-99-9 tetrahydrofuran 
• 29680-62-4 Tris(phenylseleno)borane 
• 1666-13-3 diphenyl diselenide 
• 928-51-8 4-Chloro-1-butanol 
• 33036-62-3 4-Bromo-1-butanol 
• 62559-27-7 (2-bromoethyl)phenyl selenium dibromide 
• 23768-06-1 4-(phenylseleno)butanoic acid 
• 121923-72-6 ethylphenylselenium dibromide 

Downstream Products

• 118824-28-5 3-(4-phenylselenobutanoxy)-2-methylcyclopent-2-en-1-one 
• 118824-39-8 1-bromo-4-phenylselenobutane 
• 118824-38-7 3-(4-phenylselenobutanoxy)cyclohex-2-en-1-one 
• 124854-74-6 4-(Phenylseleno)butanal 
• 1447728-66-6 C₁₂H₁₆O₂Se 
• 1447728-70-2 C₁₉H₂₀O₄Se 
• 951008-02-9 C₂₄H₂₈O₄Se 
• 1580535-22-3 C₂₄H₂₈O₄Se 
• 165687-79-6 1-Benzyl-5-(2-phenylselanyl-ethyl)-3,4-dihydro-1H-pyridin-2-one 
• 165687-75-2 methyl 4-formyl-6-selenophenylhexanoate 

Relevant academic research and scientific papers

Catalytic asymmetric claisen rearrangement of gosteli-type allyl vinyl ethers: Total synthesis of (-)-9,10-dihydroecklonialactone B

The enantioselective synthesis of (-)-9,10-dihydroecklonialactone B is described. The catalytic asymmetric Claisen rearrangement of a Gosteli-type allyl vinyl ether was utilized to afford an acyclic α-keto ester building block endowed with functionality a

On the mechanism of ylide-mediated cyclopropanations: Evidence for a proton-transfer step and its effect on stereoselectivity

In this paper, we describe studies on the cyclopropanation of Michael acceptors with chiral sulfur ylides. It had previously been found that semi-stabilized sulfonium ylides (e.g., Ph-stabilized) reacted with cyclic and acyclic enones and substituted acrylates with high ee and that stabilized sulfonium ylides (e.g., ester-stabilized) reacted with cyclic enones again with high ee. The current study has focused on the reactions of stabilized sulfonium ylides with acyclic enones which unexpectedly gave low ee. Furthermore, a clear correlation of ee with ylide stability was observed in reactions with methyl vinyl ketone (MVK): ketone-stabilized ylide gave 25% ee, ester-stabilized ylide gave 46% ee, and amide-stabilized ylide gave 89% ee. It is believed that following betaine formation an unusual proton transfer step intervenes which compromises the enantioselectivity of the process. Thus, following addition of a stabilized ylide to the Michael acceptor, rapid and reversible intramolecular proton transfer within the betaine intermediate, prior to ring closure, results in an erosion of ee. Proton transfer occurred to the greatest extent with the most stabilized ylide (ketone). When the same reactions were carried out with deuterium-labeled sulfonium ylides, higher ees were observed in all cases since proton/deuteron transfer was slowed down. The competing proton transfer or direct ring-closure pathways that are open to the betaine intermediate apply not only to all sulfur ylides but potentially to all ylides. By applying this model to S-, N-, and P-ylides we have been able to rationalize the outcome of different ylide reactions bearing a variety of substituents in terms of chemo- and enantioselectivity.

A CONVENIENT APPROACH TO THE N-SUBSTITUTED AMINO DIENES, N-BENZYL-5-ETHENYL-3,4-DIHYDROPYRIDIN-2-ONE AND N-CBZ-5-ETHENYL-1,2,3,4-TETRAHYDROPYRIDINE

A synthesis of N-substituted amino dienes (1a) and (1b) is described according to two different approaches. 1a is obtained trough condensation of methyl 4-formyl-6-selenophenylhexanoate (4) with benzylamine followed by oxidation and elimination; 1b is for

Introduction of alkyl- or phenylseleno group by the ring opening of cyclic ethers using dialkyl- or alkylphenylselenium dibromide and sodium borohydride

The reaction of dialkyl- or alkylphenylselenium dibromide with cyclic ethers in the presence of sodium borohydride gave ω-hydroxyalkyl alkyl or phenyl selenides as the ring opening products of the cyclic ethers.

Intramolecular SH2 macrocyclisations

The synthesis of 10-15 membered α-methylene macrocyclic lactones from the functionalised allylstannanes (7e)-(7j) is described. Attempts to synthesise analogous 6-9 membered lactones proved unsuccessful, resulting instead in the production of dilactones and AIBN derived adducts.

THE C-O BOND CLEAVAGE OF CYCLIC ETHERS WITH TRIS(PHENYLSELENO)BORANE-LEWIS ACID

Tris(phenylseleno)borane (1) has a hard boron element and a soft selenium element, and therefore it was expected that 1 cleaves the C-O bond.Tetrahydrofuran and tetrahydropyran were cleaved with 1 in the presence of zinc iodide to produce the δ- and ε-phe

Radical Reactions in Synthesis: Intramolecular SH2' Macrocyclisations

The synthesis of 10-15 membered α-methylene lactones 1 from the functionalised allyl stannanes 2 occurs cleanly in moderate to high yield under free radical conditions via an intramolecular SH2' reaction.

SYNTHESIS OF SPIROETHERS USING RADICAL CYCLISATIONS

A variety of spiroether products, including one bis-spiro compound, are avaible via a simple radical cyclisation route.

Preparation of γ- and δ-Phenylselenyl Alcohols via Ring Cleavage of Oxetane and Oxolane

Various types of oxetanes and oxolanes can be cleaved by reaction with phenylselenide anion prepared from diphenyl diselenide and lithium aluminum hydride in dioxane.

Cleavage of Cyclic Ethers Including Oxetane and Oxolane with a Highly Nucleophilic Species of Phenylselenide Anion

Phenylselenide anion generated from (PhSe)2 and LiAlH4 was found to be highly reactive to various types of cyclic ethers, providing a new method to prepare γ- and δ-phenylselenenyl alcohols from oxetane and oxolane, respectively.