220757-08-4

Upstream product

• 81114-98-9 Chan's diene 
• 100-52-7 benzaldehyde 
• 74590-73-1 1,3-bis(trimethylsiloxy)-1-methoxybuta-1,3-diene 
• 74590-73-1 1,3-bis(trimethylsiloxy)-1-methoxybuta-1,3-diene 
• 848900-70-9 5-(2-Chloro-acetoxy)-3-oxo-5-phenyl-pentanoic acid methyl ester 
• 682770-55-4 5-butyryloxy-3-oxo-5-phenyl-pentanoic acid methyl ester 
• 53063-63-1 5-hydroxy-3-oxo-5-phenyl-valeric acid methyl ester 
• 105-45-3 acetoacetic acid methyl ester 

Relevant academic research and scientific papers

Pronounced asymmetric amplification in the aldol condensation of Chan's diene promoted by a Ti(IV)/BINOL complex

A strong enhancement of the enantiomeric excess can be obtained by performing the enantioselective aldol reaction of Chan's diene in the presence of enantiomerically enriched Ti(O-i-Pr)4/BINOL catalysts derived from mixing pre-prepared solutions of enantiopure Ti(O-i-Pr)4/(R)-BINOL and Ti(O-i-Pr)4/(S)-BINOL at different concentrations.

An efficient asymmetric aldol reaction of Chan's diene promoted by chiral Ti(IV)-BINOL complex

1,3-Bis-(trimethylsilyloxy)-1-methoxy-buta-1,3-diene (Chan's diene) can be conveniently used in asymmetric aldol reaction with aromatic, heteroaromatic, α,β-unsaturated and aliphatic aldehydes in the presence of catalytic amounts (2-8% mol) of chiral Ti(I

An asymmetric Maitland-Japp reaction: A highly enantioselective synthesis of tetrahydropyran-4-ones

A highly enantioselective synthesis of functionalized tetrahydropyran-4- ones has been achieved by the development of a catalytic asymmetric Maitland-Japp reaction using Chan's diene as the nucleophile. This reaction has been used to synthesize the tetrah

Solvent-free asymmetric vinylogous aldol reaction of Chan's diene with aromatic aldehydes catalyzed by hydrogen bonding

Chan's diene proved to react with aromatic aldehydes under organocatalytic conditions in presence of a chiral naphthyl-TADDOL derivative to give vinylogous aldols (up to 65% ee) with complete γ-selectivity. A further process of hetero-Diels-Alder cycloadd

Enantioselective vinylogous aldol reaction of Chan's diene catalyzed by hydrogen-bonding

Hydrogen-bonding activation of aromatic aldehydes by a TADDOL-derivative promotes the vinylogous aldol reaction of Chan's diene in moderate efficiency and enantioselectivity. Electron-poor aromatic aldehydes show an enhanced reactivity and a competing asy

A new procedure for the enantioselective vinylogous aldol reaction of Chan's diene

Chiral δ-hydroxy-β-ketoesters are easily available through the enantioselective vinylogous aldol reaction of Chan's diene promoted by a SiCl4/chiral phosphoramide catalytic system. The procedure is conveniently exploited for a very rapid approach to (+)-kavain, a natural bio-active α-pyrone compound.

Candida Rugosa lipase-catalyzed kinetic resolution of β-hydroxy- β-arylpropionates and δ-hydroxy-δ-aryl-β-oxo-pentanoates

A simple and convenient method was reported for the preparation of optically active β-hydroxy-β-arylpropionates, δ-hydroxy-δ- aryl-β-oxo-pentanoates and their butyryl derivatives via CRL-catalyzed hydrolysis. The optically active products are potential precursors of some chiral pharmaceuticals and natural products.

A Chemoenzymatic Approach to Optically Active 5-Hydroxy-3-oxocarboxylates

Enzymatic hydrolysis was applied to the preparation of certain chiral 5-hydroxy-3-oxo-carboxylates that are potential precursors for natural product synthesis via the formation of lactone derivatives and tetrahydropyran rings.

Nonlinear effects and auto-induction in the asymmetric aldol condensation of synthetic equivalents of acetoacetic esters

Positive nonlinear effects, (+)-NLEs, have been detected in the Ti(IV)/BINOL complex-mediated catalytic asymmetric aldol reaction of three different masked acetoacetate esters. The use of a different procedure for the catalyst preparation disclosed the oc

A Study Directed to the Asymmetric Synthesis of the Antineoplastic Macrolide Acutiphycin under Enantioselective Acyclic Stereoselection Based on Chiral Oxazaborolidinone-Promoted Asymmetic Aldol Reactions

A shortening of the reaction path can be realized by using a series of the chiral oxazaborolidinone-promoted aldol reaction with respect to the practical synthesis of the (+)-acutiphycin seco acid derivative 5. The linear strategy is based on the utilizat