102285-76-7

Upstream product

• 1063719-01-6 3-pentanone lithium enolate 
• 100-52-7 benzaldehyde 
• 784143-65-3 (3S,1'R)-3-[(1'-hydroxy-1'-phenyl)methyl]-tetrahydrothiopyran-4-one 
• 96-22-0 pentan-3-one 
• 51425-54-8 (Z)-3-trimethylsiloxy-2-pentene 
• 17510-47-3 3-trimethylsilyloxy-2-pentene 
• 71699-16-6 (anti)-1-hydroxy-2-methyl-1-phenylpentan-3-one 
• 17042-23-8 2-iodopentan-3-one 
• 815-52-1 2-bromopentan-3-one 
• 51425-53-7 (E)-3-[(trimethylsilyl)oxy]pent-2-ene 
• 64340-78-9 ((E)-1-Ethyl-propenyloxy)-dimethyl-silane 
• 616-25-1 1-Penten-3-ol 
• 88708-63-8 Cyclohexyl-((E)-1-ethyl-propenyl)-trimethylsilanyl-amine 
• 88708-64-9 ((E)-1-Ethyl-propenyl)-octyl-trimethylsilanyl-amine 

Downstream Products

• 71699-15-5 (1R*,2R*)-1-hydroxy-2-methyl-1-phenyl-3-pentanone 
• 71699-16-6 (anti)-1-hydroxy-2-methyl-1-phenylpentan-3-one 
• 100-52-7 benzaldehyde 
• 99192-57-1 syn-1-((tert-butyldimethylsilyl)oxy)-2-methyl-1-phenylpentan-3-one 

Relevant academic research and scientific papers

ZIRCONIUM ENOLATES AS A NEW ERYTHRO-SELECTIVE ALDOL CONDENSATION REAGENT

Zirconium enolates, prepared from lithium enolates, ans bis(cyclopentadienyl)zirconium dichloride, undergo a facile aldol condensation with aldehydes to give predominantly the erythro product regardless of the geometry of the starting enolates.

Tetrahedral boronates as basic catalysts in the aldol reaction

β-Hydroxyketones are versatile building blocks in organic synthesis, which can be conveniently synthesized from ketones and aldehydes by aldol reactions. Unfortunately, these reactions often suffer from dehydration of the initially formed β-hydroxyketones

Rh-catalyzed aldehyde - Aldehyde cross-aldol reaction under base-free conditions: In situ aldehyde-derived enolate formation through orthogonal activation

The chemoselective generation of aldehyde-derived enolates to realize an aldehyde - aldehyde cross-aldol reaction is described. A combined Rh/dippf system efficiently promoted the isomerization/aldol sequence by using primary allylic, homoallylic, and bishomoallylic alcohols; secondary allylic and homoallylic alcohols; and trialkoxyboranes that were derived from primary allylic and homoallylic alcohols. The reaction proceeded at ambient temperature under base-free conditions, thus giving cross-aldol products with high chemoselectivity. Mechanistic studies, as well as its application to double-aldol processes under protecting-group-free conditions, are also described. Copyright

Rhodium-catalyzed cross-aldol reaction: In situ aldehyde-enolate formation from allyloxyboranes and primary allylic alcohols

Dip in. A Rh/dippf catalyst generates aldehyde-derived enol boranes at ambient temperature by isomerization of allyloxy- and homoallyloxyboranes. A one-pot isomerization/cross-aldol sequence provides aldehyde-aldehyde adducts in good yield with syn select

Synthesis of (+)-discodermolide by catalytic stereoselective borylation reactions

The marine natural product (+)-discodermolide was first isolated in 1990 and, to this day, remains a compelling synthesis target. Not only does the compound possess fascinating biological activity, but it also presents an opportunity to test current methods for chemical synthesis and provides an inspiration for new reaction development. A new synthesis of discodermolide employs a previously undisclosed stereoselective catalytic diene hydroboration and also establishes a strategy for the alkylation of chiral enolates. Furthermore, this synthesis of discodermolide provides the first examples of the asymmetric 1,4-diboration of dienes and borylative diene-aldehyde couplings in complex-molecule synthesis. Borylation-based synthesis: The development of a strategy for stereocontrol in catalytic diene hydroboration enables the synthesis of a critical building block for the assembly of (+)-discodermolide. Combined with asymmetric catalytic diboration, hydroformylation, and borylative aldehyde-diene coupling reactions, (+)-discodermolide could then be prepared from simple hydrocarbon-based building blocks.

STEREOSELECTIVE ALDOL CONDENSATIONS VIA ALKENYLOXY DIALKYOXYBORANES: MECHANISTIC AND STEREOCHEMICAL DETAILS.

A detailed investigation of the enolization of ketones with ethylenechloroboronate (ECB) in the presence of a tertiary amine and the subsequent aldol condensations of these boron enolates was conducted.The enolization with ECB-DPEA system was found to be

STEREOSELECTIVE ALDOL CONDENSATIONS VIA ENOLBORONATES

Enolboronates, new enolates directly accessible from carbonyl compounds, exhibit extraordinary high erythro diastereoselection both with aliphatic and aromatic aldehydes.

erythro-Selective Aldol Condensation via Triphenyltin Enolates. Stereoselection Independent of the Stereochemistry of the Enolates

Triphenyltin enolates, prepared from lithium enolates and triphenyltin chloride, undergo a rapid aldol condensation with aldehydes without the need for the presence of Lewis acids to give predominantly the erythro-product regardless of the geometry of the starting enolates.

Novel Reactive Silyl Enolates. Highly Stereoselective Aldol and Michael Reactions without Catalysts

Novel silyl enolates, prepared in situ from ketones and dimethylsilyl ditriflate (Me2Si(OTf)2) in the presence of a tertiary amine, reacted smoothly with electrophiles such as aldehydes, acetals, or α,β-unsaturated ketones without catalyst at -78 deg C to

Zn(pybox)-complex-catalyzed asymmetric aqueous Mukaiyama-Aldol reactions

Catalytic asymmetric aldol reactions in aqueous media have been developed using chiral zinc complex. The aldol products have been obtained in high yields, high diastereocontrol, and good level of enantioselectivity. Various aromatic and α,β-unsaturated al