188924-71-2

Upstream product

• 58479-61-1 tert-butylchlorodiphenylsilane 
• 178246-78-1 (R)-3-(tert-Butyldiphenylsilanyloxy)butyric acid methyl ester 
• 577743-41-0 (R)-2-Hydroxy-4-methyl-5-phenylpent-4-ene 
• 577743-79-4 (+)-[(1E,4R)-4-(tert-butyldiphenylsilyloxy)-2-methylpent-1-enyl]benzene 
• 917-54-4 methyllithium 
• 147963-64-2 (R)-3-[(tert-butyl)diphenylsilyloxy]butanoic acid 
• 75-16-1 methylmagnesium bromide 
• 183310-90-9 (R)-3-(tert-butyl-diphenyl-silanyloxy)-butyraldehyde 

Downstream Products

• 188924-72-3 (R)-6-(tert-Butyl-diphenyl-silanyloxy)-1-((2S,4S,6S)-6-methyl-2-phenyl-[1,3]dioxan-4-yl)-heptane-2,4-dione 
• 188924-81-4 (R)-6-Hydroxy-1-((2S,4S,6S)-6-methyl-2-phenyl-[1,3]dioxan-4-yl)-heptane-2,4-dione 
• 188924-80-3 (R)-6-(tert-Butyl-diphenyl-silanyloxy)-2-hydroxy-1-((2S,4R,6S)-6-methyl-2-phenyl-[1,3]dioxan-4-yl)-heptan-4-one 

Relevant academic research and scientific papers

Catalytic reductive carbon-carbon bond-forming reactions of alkynes

Enantioselective nickel/phosphine-catalyzed reductive coupling of alkynes and aldehydes provides rapid access to synthetically useful allylic alcohols with high enantiomeric excess. A related reaction involving epoxides is enantiospecific, transforming al

Nickel-catalyzed reductive coupling of alkynes and epoxides

Nickel-catalyzed, intramolecular and intermolecular reductive coupling of alkynes and epoxides affords synthetically useful homoallylic alcohols of defined alkene geometry. Very high regioselectivity is generally observed, and cyclizations proceed with complete selectivity for endo epoxide opening. This catalytic reaction represents the first use of a non-π-based electrophile in a growing class of nickel-catalyzed, multicomponent coupling reactions, and is the first catalytic method of reductive coupling of alkynes and epoxides that is effective for both intermolecular and intramolecular cases, and mechanistically distinct from these, possibly involving a nickella(II)oxetane. Copyright

Synthesis of Enantiopure Homoallylic Ethers by Reagent Controlled Facial Selective Allylation of Chiral Ketones

The stereoselective allylation of chiral methyl ketones to give tertiary homoallylic ethers, which can easily be transformed into homoallylic alcohols, is described. Reaction of the enantiopure ketones 8a-d and the racemic ketones 26a-d with the norpseudoephedrine derivative 2 or ent-2 and allylsilane in the presence of a catalytic amount of trifluoromethanesulfonic acid, led to a series of homoallylic ethers with good to excellent diastereoselectivity (85:15 to > 97:3). The allylation is reagent controlled and nearly independent from the stereogenic centers in the substrates. A partial kinetic resolution was observed using the racemic ketones 26a-d. In the reaction of the chiral ketones 8a-d with the achiral reagents ethoxytrimethylsilane and allylsilane only a low diastereoselectivity was observed.