879005-60-4

Upstream product

• 459-57-4 4-fluorobenzaldehyde 
• 107-05-1 3-chloroprop-1-ene 
• 24850-33-7 allyltributylstanane 
• 108-22-5 Isopropenyl acetate 
• 86718-78-7 1-(4-fluorophenyl)-3-buten-1-ol 
• 106-95-6 allyl bromide 
• 762-72-1 allyl-trimethyl-silane 
• 107-37-9 allyltrichlorosilane 
• 555-16-8 4-nitrobenzaldehdye 
• 75-77-4 chloro-trimethyl-silane 

Downstream Products

• 795306-57-9 3′-(S)-4-(S)-3-(R)-[3′-t-butyldimethylsilyloxy-3′-(4-fluorophenyl)propyl]-4-(4-hydroxyphenyl)-1-(4-fluorophenyl)azetidin-2-one 
• 1392303-25-1 tert-butyl (2R,4S)-(+)-2-(4-fluorophenyl)-6-oxotetrahydro-2H-pyran-4-yl-carbamate 
• 1392303-20-6 methyl (3S,5R)-(+)-3-(tert-butoxycarbamoyl)-5-hydroxy-5-(4-fluorophenyl)valerate 
• 1392303-06-8 (3S,5R)-(+/-)-N-tert-butoxycarbonyl-3-(methoxycarbonylmethyl)-5-(4-fluorophenyl)isoxazolidine 
• 1392302-95-2 (R)-(+)-tert-butyl {[1-(4-fluorophenyl)-3-butene-1-yl]oxy}carbamate 
• 1392302-85-0 (R)-(+)-O-[1-(4-fluorophenyl)-3-butene-1-yl]hydroxylamine 

Relevant academic research and scientific papers

Chiral bipyridine-annulated bicyclo[3.3.1]nonane N-oxide organocatalysts for stereoselective allylation and hydrosilylation reactions

The synthesis of chiral C2-symmetric bis(bipyridine N,N′-dioxide) and bis(bipyridine N-monooxide) derivatives featuring bipyridine-annulated bicyclo[3.3.1]nonane framework is reported. The new Lewis basic bipyridine N,N′-dioxides exhibited good

Highly Enantioselective Allylation Reactions of Aldehydes with Allyltrimethylsilane Catalyzed by a Chiral Oxazaborolidinium Ion

A highly enantioselective allylation reaction of aldehydes with silyl reagents was developed for the synthesis of a variety of chiral homoallylic alcohols. In the presence of a chiral oxazaborolidinium ion (COBI) catalyst, the reaction proceeded in high yield (up to 99percent) with excellent asymmetric induction (up to 99percent ee).

Axially chiral N,N′-dioxides ethers for catalysis in enantioselective allylation of aldehydes

A series of axially chiral ethers synthesized from biscarboline N,N′-dioxides, (S)-1a to (S)-1n, was investigated in enantioselectivity addition reactions of allyltrichlorosilane with a series of substituted aldehydes, including bulky substituted aldehydes. High enantioselectivities (up to 96%ee) were achieved using the catalyst (S)-1k at 1 mol % loading.

Chiral Bisdiphenylphosphine Dioxides Bearing a Bis(triazolyl) Backbone as Promising Lewis Bases for Asymmetric Organocatalysis

Two chiral C2-symmetric diphenylphosphine dioxides bearing an original bis(triazolyl) backbone were prepared starting from inexpensive and readily available precursors. The key step involves the simultaneous formation of five bonds in one chemi

Oxazoline derivatives tagged with tosylated amino acids as recyclable organocatalysts for enantioselective allylation of aldehydes

A series of amino acid-based oxazoline compounds have been prepared and successfully applied to the enantioselective allylation reaction of aldehydes. The fine-tuning of the structure of the oxazolines led to (S,S)-4 as an efficient organocatalyst which gave homoallyl alcohols in good yield (up to 90%) and excellent ee (up to 99%) for a wide range of substrates including aromatic, hetero-aromatic and α,β-unsaturated aldehydes. The chiral organocatalyst was synthesized in three easy steps with an overall 88% yield and successfully recycled for up to three cycles. On the basis of the experimental observations and NMR studies, a probable mechanism was proposed for this reaction.

Dynamic kinetic resolution of homoallylic alcohols: Application to the synthesis of enantiomerically pure 5,6-dihydropyran-2-ones and δ-lactones

Dynamic kinetic resolution of various homoallylic alcohols with the use of Candida antarctica lipase B and ruthenium catalyst 2 afforded homoallylic acetates in high yields and with high enantioselectivity. These enantiopure acetates were further transfor

Synthetically amenable amide derivatives of tosylated-amino acids as organocatalysts for enantioselective allylation of aldehydes: Computational rationale for enantioselectivity

A phenylalanine derived chiral amide is developed that serves as an effective organocatalyst for the reaction of allyltrichlorosilane with aryl, hetero-aryl and α,β-unsaturated aldehydes to afford the desired homoallylic alcohols in good yield (up to 90%)

Addition of aldehydes with allyltrichlorosilane catalyzed by chiral bis-N-O secondary amides

New axially N-oxide amides derived from l-tryptophan were prepared and used as organocatalysts in enantioselective allylation of aromatic aldehydes with allyltrichlorosilanes. The corresponding addition adducts homoallylic chiral alcohols obtained high en

An efficient route for the allylation of arylaldehydes to give enantiopure homoallylic alcohols

An efficient asymmetric synthesis of homoallylic alcohols is described by the allylation of carbonyl compounds using organocatalysts as chiral directors in the presence of tin metal. The effect of chiral environment is also studied on the allylation reactions. This method allows us to obtain two different enantiomers of homoallylic alcohol in the presence of the corresponding chiral compound. The protocol is applied to various aldehydes to obtain high yields and excellent enantioselectivities for the corresponding homoallylic alcohols.

Mechanistic dichotomy in the asymmetric allylation of aldehydes with allyltrichlorosilanes catalyzed by chiral pyridine N-oxides

Detailed kinetic and computational investigation of the enantio- and diastereoselective allylation of aldehydes 1 with allyltrichlorosilanes 5, employing the pyridine N-oxides METHOX (9) and QUINOX (10) as chiral organocatalysts, indicate that the reaction can proceed through a dissociative (cationic) or associative (neutral) mechanism: METHOX apparently favors a pentacoordinate cationic transition state, while the less sterically demanding QUINOX is likely to operate via a hexacoordinate neutral complex. In both pathways, only one molecule of the catalyst is involved in the rate- and selectivity-determining step, which is supported by both experimental and computational data. Copyright