138509-95-2

Upstream product

• 100-52-7 benzaldehyde 
• 138509-94-1 (Z)-1-(ethylthio)-1-(trimethylsiloxy)-2-(tert-butyldimethylsiloxy)ethene 
• 160114-64-7 S-ethyl 2-(t-butyldimethylsiloxy)ethanethioate 
• 18162-48-6 tert-butyldimethylsilyl chloride 
• 105459-05-0 {[tert-butyl(dimethyl)silyl]oxy}acetic acid 
• 78826-45-6 2-((tert-butyldimethylsilyl)oxy)acetyl chloride 
• 67226-76-0 (tert-butyldimethylsiloxy) acetic acid tert-butyldimethylsilyl ester 
• 67226-78-2 ethyl 2-(tert-butyldimethylsilyloxy)acetate 

Relevant academic research and scientific papers

Anti-selective asymmetric aldol reactions. Enantioselective synthesis of anti-αβ-dihydroxy phenyl ester derivatives

In the presence of a chiral tin(II) Lewis acid, the silyl enol ether derived from (E)-phenyl α-t-butyldimethylsiloxyacetate reacted with aldehydes to afford the corresponding anti-aldol adducts, anti-α,β-dihydroxy ester derivatives, in high yields with hi

Chiral Lewis acid controlled synthesis (CLAC synthesis): Chiral Lewis acids influence the reaction course in asymmetric aldol reactions for the synthesis of enantiomeric dihydroxythioester derivatives in the presence of chiral diamines derived from L-prol

Both enantiomers of 2,3-dihydroxythioester derivatives were prepared with almost perfect stereochemical control by chiral Lewis acid controlled synthesis (CLAC synthesis). CLAC synthesis means synthesis of all individual diastereomers or enantiomers from

Preparation of both enantiomers of 2-methyl-3-hydroxythioesters based on chiral Lewis acid-controlled synthesis

Both enantiomers of 2-methyl-3-hydroxythioesters have been synthesized by using chiral tin(II) Lewis acid-mediated aldol reactions of (Z)-1-ethylthio-1-trimethylsiloxypropene (4) with aldehydes, based on chiral Lewis acid-controlled synthesis. The key to

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.

Molecular recognition by artificial chiral catalysts utilizing a metal chelate. A remarkable difference in reactivity between geometrical isomers of silyl enolates in asymmetric aldol reactions using chiral Tin(II) catalysts

A remarkable difference in reactivity between (E)- and (Z)-enolates in the asymmetric aldol reactions of silyl enolates with adehydes using chiral tin(II) Lewis acids was found. This difference can be interpreted to mean that the chiral catalyst coordinat

Diastereo- and Enantioselective Synthesis of syn- and anti-1,2-Diol Units by Asymmetric Aldol Reactions

syn- and anti-1,2-Diol units were prepared by using asymmetric aldol reactions of the silyl enol ethers derived from α-alkoxythioacetic S-esters with aldehydes.In the presence of tin(II) triflate, a chiral diamine, and dibutyltin diacetate, (Z)-2-benzyloxy-1-ethylthino-1-(trimethylsiloxy)ethene reacted with aldehydes to afford the corresponding anti-aldol adducts in high yields with excellent diastereo- and enantioselectivities, while syn-adducts were obtained from (Z)-2-(t-butyldimethylsiloxy)-1-ethylthio-1-(trimethylsiloxy)ethene and aldehydes under the same reaction conditions.Thus, both diastereomers can be synthesized in excellent enantiomeric excesses by simply choosing the protective groups of the alkoxyl parts of the silyl enol ethers.

Enantioselective synthesis of both diastereomers including the α-alkoxy-β-hydroxy-β-methyl(phenyl) units, by chiral tin(II) Lewis acid-mediated asymmetric aldol reactions

Diastereo- and enantioselective synthesis of both diasteromers, including the α-alkoxy-β-hydroxy-β-methyl(phenyl) units, was performed by using chiral tin(II) Lewis acid-mediated asymmetric aldol reactions of α-alkoxy silyl enol ethers with α-ketoesters. (S)-1-Propyl-2-[(1,2,3,4-tetrahydroisoquinolinyl))methyl]pyrrolidine (13), a new type of chiral diamine, was found to be effective as a chiral source in these reactions and also in the reactions of 2-(t-butyldimethylsiloxy)-1-ethylthio-1-(trimethylsiloxy)ethene (9) with aldehydes for the synthesis of optically active syn-α,β-dihydroxy thioester derivatives. (-)-2-C-Methyl-D-erythrono-1,4-lactone and (+)-2-C-methyl-L-threono-1,4-lactone were synthesized by using these reactions.

Highly Enantioselective Synthesis of syn-α,β-Dihydroxy Thioesters by the Asymmetric Aldol Reaction Using a Chiral Tin(II) Lewis Acid

syn-α,β-Dihydroxy thioesters are prepared in good yields with high diastereo- and enantioselectivities by the asymmetric aldol reaction of 1-trimethylsiloxy-1-ethylthio-2-t-butyldimethylsiloxyethene with aldehydes using a chiral promoter consisting of tin(II) triflate, a chiral diamine and dibutyltin diacetate.