221898-37-9

Upstream product

• 24850-33-7 allyltributylstanane 
• 1122-91-4 4-bromo-benzaldehyde 
• 1730-25-2 allylmagnesium bromide 
• 107-37-9 allyltrichlorosilane 
• 762-72-1 allyl-trimethyl-silane 
• 72824-04-5 2-Allyl-4,4,5,5-tetramethyl-1,3,2-dioxaborolane 
• 106-95-6 allyl bromide 
• 108-22-5 Isopropenyl acetate 
• 106650-98-0 1-(4-bromophenyl)but-3-en-1-ol 
• 55137-94-5 triallyltin bromide 
• 591-87-7 Allyl acetate 
• 873-75-6 4-bromobenzenemethanol 

Downstream Products

• 913626-19-4 3-[(1S)-1-(4-bromo-phenyl)-but-3-enyloxy]-propionitrile 
• 1392302-86-1 (R)-(+)-O-[1-(4-bromophenyl)-3-butene-1-yl]hydroxylamine 
• 1392302-96-3 (R)-(+)-tert-butyl {[1-(4-bromophenyl)-3-butene-1-yl]oxy}carbamate 
• 1392303-07-9 (3S,5R)-(+/-)-N-tert-butoxycarbonyl-3-(methoxycarbonylmethyl)-5-(4-bromophenyl)isoxazolidine 
• 913626-29-6 C₆₅H₁₁₇BrO₁₄Si₄ 
• 913626-18-3 Octanoic acid (E)-(1S,5S,9S,11S,15R,19R,21S,24S)-11-(4-bromo-phenyl)-1,15-dihydroxy-19-hydroxymethyl-23-[1-methoxycarbonyl-meth-(E)-ylidene]-2,2-dimethyl-17-oxo-6,12,18,25,26-pentaoxa-tricyclo[19.3.1.1^5,9]hexacos-3-en-24-yl ester 
• 1026938-43-1 5-[1-(4-bromo-phenyl)-3,5-bis-(tert-butyl-dimethyl-silanyloxy)-pentyloxy]-3-(tert-butyl-dimethyl-silanyloxy)-pentanoic acid 
• 913626-22-9 (3R,5S)-5-(4-Bromo-phenyl)-5-((R)-4-tert-butoxycarbonyl-3-hydroxy-butoxy)-3-hydroxy-pentanoic acid ethyl ester 
• 913626-21-8 5-(4-bromo-phenyl)-5-(4-tert-butoxycarbonyl-3-oxo-butoxy)-3-oxo-pentanoic acid ethyl ester 
• 913626-28-5 (R)-5-[(1S,3S)-1-(4-Bromo-phenyl)-3,5-dihydroxy-pentyloxy]-3-hydroxy-pentanoic acid tert-butyl ester 
• 913626-20-7 5-[1-(4-bromo-phenyl)-but-3-enyloxy]-3-oxo-pentanoic acid tert-butyl ester 

Relevant academic research and scientific papers

A chiral oxazoline for catalytic enantioselective Nozaki-Hiyama-Kishi allylation and vinylation of aldehydes

Asymmetric allylation and vinylation of aldehydes with allyl halides and vinyl halides have been achieved using the chromium(II)-oxazoline catalyst. The catalyst promotes the highly efficient enantioselective Nozaki–Hiyama-Kishi (NHK) allylation of aldehydes using allyl bromide, producing the corresponding homoallylic alcohols in good yields (up to 84%) and a high level of enantioselectivity (up to 98% ee). Meanwhile, the NHK vinylation of aldehydes produce desired allylic alcohols in satisfactory yields (up to 88%) and a high level of enantioselectivity (up to 97% ee). We developed a reliable and milder protocol for preparing chiral homoallylic and allylic alcohols.

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).

Enantioselective Allyl-, and Allenylboration of Aldehydes Catalyzed by Chiral Hydroxyl Carboxylic Acid

Asymmetric allylboration of aldehydes with allylboronic acid pinacol ester catalyzed by chiral hydroxyl carboxylic acid is described. This reaction provides synthetically useful homoallyl alcohols in high yield with good to high enantioselectivity. The pr

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%)

Asymmetric synthesis of novel axially chiral 2,2′-bipyridine n,n′-dioxides bearing α-amino acid residues and their applications in enantioselective allylation of aromatic aldehydes with allyltrichlorosilane

A series of novel axially chiral 2,2′-bipyridine N,N′-dioxides bearing C1 or C2-symmetry have been synthesized by the use of enantiopure α-amino acids as chiral sources. The absolute stereochemistry of the axial chirality of these or

Chiral bis(imidazolinyl)phenyl NCN pincer rhodium(III) Catalysts for enantioselective allylation of aldehydes and carbonyl-ene reaction of trifluoropyruvates

Chiral NCN pincer rhodium(III) complexes with bis(imidazolinyl)phenyl ligands were found to be effective catalysts for the allylation of a variety of electronically and structurally diverse aldehydes with allyltributyltin, giving the corresponding optical

Practical, highly stereoselective allyl- and crotylsilylation of aldehydes catalyzed by readily available Cinchona alkaloid amide

We have demonstrated that bidentate Lewis base catalysts can be constructed based on the Cinchona alkaloid structure that promote highly stereoselective reactions of allyl- and crotyltrichlorosilane with aromatic as well as aliphatic aldehydes (90-99% ee, >98% diastereoselectivity). The catalysts are available in a one-pot procedure in >70% yield from cheap starting materials and promote the allylation reactions at ambient temperature. Gram scale reactions with catalyst recovery and reuse showcased the practicality of the catalytic system.

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.

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

Stereoselective palladium-catalyzed functionalization of homoallylic alcohols: A convenient synthesis of di- and trisubstituted isoxazolidines and β-amino-δ-hydroxy esters

Enantiopure, Boc-protected alkoxyamines 12 and 13, derived from the readily available homoallylic alcohols 4 via a reaction that involves either inversion or retention of configuration, undergo a diastereoselective Pd-catalyzed ring-closing carbonylative