123166-63-2

Upstream product

• 63584-41-8 1-ethylthio-1-(trimethylsiloxy)ethene 
• 100-52-7 benzaldehyde 
• 175227-23-3 (S)-3-((R)-3-Hydroxy-1-methyl-propoxy)-3-phenyl-thiopropionic acid S-ethyl ester 
• 79464-76-9 (2S,4R)-4-methyl-2-phenyl-1,3-dioxane 
• 175227-33-5 (S)-3-((R)-1-Methyl-3-oxo-propoxy)-3-phenyl-thiopropionic acid S-ethyl ester 

Relevant academic research and scientific papers

A novel chiral zirconium catalyst for enantioselective aldol and Mannich-type reactions. Catalytic activation of both aldehydes and imines using a similar chiral Lewis acid

A novel zirconium catalyst has been developed for asymmetric aldol reaction of aldehydes with silyl enolates and asymmetric Mannich reactions of imines with silyl enolates. Similar types of catalysts have been successfully used in both reactions, and the

Highly anti-selective asymmetric aldol reactions using chiral zirconium catalysts. Improvement of activities, structure of the novel zirconium complexes, and effect of a small amount of water for the preparation of the catalysts

Catalytic asymmetric aldol reactions of silyl enol ethers with aldehydes (Mukaiyama aldol reactions) have been performed using novel chiral zirconium catalysts. The reactions proceeded in high yields under mild conditions, and anti-adducts were obtained i

Asymmetric Synthesis of Functionalized Secondary Alcohols by Catalytic Ring-Cleavage Reactions of Cyclic Acetals Derived from (R)-1,3-Butanediol

In the presence of a catalytic amount (0.1-0.2 molar amount) of a 2-phenyl-1,3,2-oxazaborolidin-5-one, prepared by the reaction of dichlorophenylborane and N-(trifluoromethylsulfonyl)-L- phenylalanine, and enol silyl ethers ((R2)2C=C-(R3)OTMS; R3 = t-BuS, EtS, EtO, Ph) (1.1-1.5 molar amount), chiral cyclic acetals 6 derived from (R)-1,3-butanediol and aldehydes undergo an efficient ring-cleavage reaction with the inversion of the stereochemistry at the acetal carbon to give the anti isomer of the corresponding products with high stereoselectivity. The reaction is applicable to acetals derived from aromatic, aliphatic, and α,β-unsaturated aldehydes. Not only enol silyl ethers, but also methallyltrimethylsilane and allyltributyltin, can be employed as nucleophiles, leading to the selective formation of the anti isomer of the corresponding allylated ring-cleavage products. Removal of the chiral auxiliary from these ring-cleavage products by a two-step sequence ((i) PCC (ii) Bn2NH2(CF3CO2)) furnishes enantiomerically enriched β-hydroxy carbonyl compounds and homoallyl alcohols. A modest level of kinetic resolution is observed in the ring cleavage of a racemic acetal catalyzed by a phenylboron compound derived from N-mesyl-L-phenylalanine.

Chiral tin(II) Lewis acid-mediated enantioselective aldol reactions: Synthesis of both enantiomers using similar types of chiral sources

Chiral tin(II)-Lewis acid-mediated aldol reactions of various enolates with an aldehyde were investigated by using chiral diamine 2. Based on these reactions, both enantiomers of aldol adducts were prepared using similar types of chiral sources.

The catalytic asymmetric aldol reaction of aldehydes with unsubstituted and monosubstituted silyl ketene acetals: Formation of anti-β-hydroxy-α-methyl esters

The title rection with unsubstituted and monosubstituted silyl ketene acetals proceeds with high enantioselectivity, and in the latter case good diastereoselectivity favoring the anti-β-hydroxy-α-methyl esters in all reported cases.

Asymmetric Aldol Reaction between Achiral Silyl Enol Ethers and Achiral Aldehydes by Use of a Chiral Promoter System

In the presence of a chiral promoter consisting of tin(II) triflate, a chiral diamine, and tributyltin fluoride, the silyl enol ether of S-ethyl ethanethioate or S-tert-butyl ethanethioate reacts with aldehydes to afford the corresponding aldol-type adduc

New role of tin(II) compounds in organic synthesis

Three new carbon-carbon bond forming reactions by the use of new catalyst systems involving tin(II) compounds are described in this article.The aldol reaction of silyl enol ethers with acetals or aldehydes and the Michael reaction of silyl enol ethers wit

ASYMMETRIC ALDOL REACTION OF SILYL ENOL ETHERS WITH ALDEHYDES PROMOTED BY THE COMBINED USE OF CHIRAL DIAMINE COORDINATED TIN(II) TRIFLATE AND TRIBUTYLTIN FLUORIDE

Asymmetric aldol reaction of silyl enol ethers of thioesters with aldehydes is performed in high enantiomeric excess by the use of a new chiral promoter, a combined use of chiral diamine coordinated tin(II) triflate and tributyltin fluoride.