19641-54-4

Upstream product

• 693-04-9 butyl magnesium bromide 
• 98-86-2 acetophenone 
• 1009-14-9 phenyl butyl ketone 
• 544-97-8 dimethyl zinc(II) 
• 191479-34-2 (+/-)-2-phenylhex-2-yl hydroperoxide 
• 591-78-6 n-hexan-2-one 
• 16635-23-7 phenyltriisopropoxytitanium(IV) 
• 80441-29-8 (SS)-1-(N-methylphenylsulfonimidoyl)-2-phenyl-2-hexanol 
• 109-72-8 n-butyllithium 
• 141765-56-2 1-methyl-1-phenyl-1,5-pentanediol 
• 131342-12-6 (S)-1-((S)-Naphthalene-1-sulfinyl)-2-phenyl-hexan-2-ol 

Relevant academic research and scientific papers

First enantioselective addition of diethylzinc and dimethylzinc to prostereogenic ketones catalysed by camphorsulfonamide-titanium alkoxide derivatives

The reaction of diethylzinc or dimethylzinc with prostereogenic ketones, in the presence of a stoichiometric amount of titanium tetraisopropoxide and a catalytic amount (20%) of camphorsulfonamide derivatives as chiral ligands leads to the formation of the corresponding enantioenriched tert-alcohols with enantiomeric ratios up to 94.5 : 5.5. the best results were obtained when phenones are used as substrates independently of the dialylzinc reagent. The enantioselectivity shows a linear relationship with the enantiomeric excess of the ligand and seems to be independent of the reaction yield. A tentative catalytic cycle and mechanistic model are proposed for this new reaction.

Enantioface-differentiating Addition of Butyllithium to Acetophenone by the Use of ((1S,2S,5S)-3--2-pinanols as Chiral Ligands

Butyllithium and acetophenone gave optically active 2-phenyl-2-hexanol (33percent e.e.) in good yield in the presence of (1S,2S,5S)-3-2-pinanol (1).

MgBr2-promoted enantioselectIVe aryl addition of ArTi(OiPr)3 to ketones catalyzed by a titanium(IV) catalyst of N,N′-sulfonylated (1R,2R)-cyclohexane-1,2-diamine

MgBr2-promoted asymmetric addition of ArTi(OiPr)3 to ketones catalyzed by a titanium catalyst of N,N′-sulfonylated (1R,2R)-cyclohexane-1,2-diamines is reported, and results showed that the chiral N,N′-sulfonylated cyclohex

Kinetic resolution of hydroperoxides with enantiopure phosphines: Preparation of enantioenriched tertiary hydroperoxides

An efficient reductive kinetic resolution strategy capable of accessing optically active tertiary hydroperoxides is reported. Readily accessible tertiary hydroperoxides are resolved with commercially available (R)- or (S)-xylyl-PHANEPHOS with selectivity factors as large as 37. The resulting bis(phosphine oxide) can be recycled in high yields. The isolated mono(phosphine oxide) intermediate resolved hydroperoxides with the same selectivity as the parent bisphosphine. Copyright

Catalytic asymmetric addition of alkylzinc and functionalized alkylzinc reagents to ketones

(Chemical Equation Presented) We describe our full report of the catalytic asymmetric addition of simple and functionalized dialkylzinc reagents to a broad range of saturated ketones and enones. The functionalized organozinc reagents contain esters, silyl

A green chemistry approach to a more efficient asymmetric catalyst: Solvent-free and highly concentrated alkyl additions to ketones

There is a great demand for development of catalyst systems that are not only efficient and highly enantioselective but are also environmentally benign. Herein we report investigations into the catalytic asymmetric addition of alkyl and functionalized alk

Efficient 1,8- and 1,9-asymmetric inductions in the Grignard reaction of δ- and ε-keto esters of 1,1′-binaphthalen-2-ols with an oligoether tether as the 2′-substituent: Application to the synthesis of (-)-malyngolide

Efficient 1,8- and 1,9-asymmetric inductions in the Grignard reaction of podand-type δ- (3,4) and ε-keto esters (5,6) are achieved in the presence of MgBr2·OEt2 with up to 97 and 82% optical yields, respectively, by using 2′-[3-(2-methoxyethoxy)propoxy]-1,1′-binaphthalen-2-ol as the chiral auxiliary. The 1,8-asymmetric inductive Grignard reaction has been advantageously utilized in the key step of a synthesis of (-)-malyngolide.

First enantioselective addition of dialkylzinc to ketones promoted by titanium(IV) derivatives

The reaction of dimethyl or diethylzinc with ketones in the presence of a stoichiometric amount of titanium tetraisopropoxide and a catalytic amount (20 mol %) of camphorsulfonamide derivatives as chiral ligands leads to the formation of the corresponding

Highly enantioselective addition of primary alkyl Grignard reagents to carbocyclic and heterocyclic arylketones in the presence of magnesium TADDOLate preparative and mechanistic aspects

In the presence of equimolar amounts of the Mg alkoxide from α,α,α',α'-tetraphenyl-2,2-dimethyl-1,3-dioxolan-4,5-dimethanol (a TADDOL) primary Grignard reagents (Et, Pr, Bu, Oct, 3-butenyl) add to carbo- and heteroaromatic methyl ketones in THF at -100°C to give tertiary alcohols of enantiomeric excesses reaching values above 98%. The scope and limitation of the method are investigated. The reaction, which occurs in a vigorously stirred heterogeneous mixture, give best results in the absence of steric hindrance of the reacting centers; Grignard reagents made from alkyl bromides are superior to those obtained from chlorides; there is a perfect linear relationship between the ee of the TADDOL and of the product 2-phenyl-2-decanol; those tertiary alcohols of which the absolute configuration is known, are formed by nucleophilic attack from the Re face of the keto carbonyl groups. Three tentative mechanistic models for the stereochemical course of the reaction are discussed.

HIGHLY ENANTIOSELECTIVE ADDITION OF (S)-LITHIOMETHYL 1-NAPHTHYL SULFOXIDE TO KETONES

The anion of (S)-(-)-methyl 1-naphthyl sulfoxide reacts enantioselectively with alkyl phenyl ketones to give (SsSc)-β-hydroxysulfoxides with diastereomeric excess (de) up to 100percent.Optical pure (S)-tertiary alcohols are prepared by desulfurization of the corresponding diastereomers.