65878-64-0

Upstream product

• 10467-10-4 ethylmagnesium iodide 
• 93-53-8 (S)-2-phenyl-propionaldehyde 
• 34713-70-7 2-Phenylpropanal 
• 63801-22-9 2-phenylpentan-3-one 
• 2397-68-4 sodium tetraethylaluminate 
• 78-00-2 tetraethyllead(IV) 
• 557-20-0 diethylzinc 
• 925-90-6 ethylmagnesium bromide 

Downstream Products

• 75724-31-1 (+/-)-threo-3-(3.5-dinitro-benzoyloxy)-2-phenyl-pentane 
• 127181-69-5 (2R,3R)-erythro-2-phenylpentan-3-ol 
• 24663-49-8 DL-erythro-2-Phenyl-pentyl-⁽³⁾-methansulfonat 
• 75724-23-1 cyclohexyl-2 pentanol-3 
• 75724-23-1 cyclohexyl-2 pentanol-3 

Relevant academic research and scientific papers

Kinetic resolution when the chiral auxiliary is not enantiomerically pure: Normal and abnormal behavior

Kinetic resolutions with enantioimpure chiral auxiliaries (reagents or catalysts) are considered, and a kinetic treatment for various rate laws is described. A useful parameter, the apparent stereoselectivity factor, is defined and correlated to the enantiomeric excess of the chiral auxiliary. Deviations from the regular laws are possible (asymmetric amplification or depletion). These anomalies have their origins in the same phenomena that cause nonlinear effects in enantioselective catalysis. Asymmetric amplifications have been experimentally observed.

[1,2]-Wittig rearrangement of enantio-defined α-alkoxyalkyllithiums: Structural requirement and steric course at the Li-bearing terminus

The [1,2]-Wittig rearrangements of enantio-defined α-benzyloxypropyllithium and its (R)-α-methylbenzyloxy analogs, generated from the enantio-enriched stannanes via Sn/Li exchange, are shown to proceed predominantly with inversion of configuration at the

[1,2]-Wittig rearrangement of enantio-defined α-alkoxyalkyllithiums: Stereochemistry at the Li-bearing terminus and mutual recognition of enantiomers during the radical recombination

The [1,2]-Wittig rearrangements of enantio-defined α-benzyloxypropyllithium and its (R)-α-methylbenzyloxy analogs, generated from the enantio-enriched stannanes via Sn/Li exchange, are shown to proceed predominantly with inversion of configuration at the

A new type of complex reagent, R4Pb / TiCl4

Tetraalkllleads (R4Pb) reacted quite smoothly with aldehydes R'CHO in the presence of TiCl4 to produce the corresponding alcohols (RCHOHR′) in high to good yields. The reagent system, R4Pb/ TiCl4, exhibited high chemoselectivity; only aldehydes underwent the alkylation in the presence of ketones. Further, the new reagent exhibited high 1,2- and 1,3-asymmetric induction. The transfer order of alkyl groups in the reaction of aldehydes with mixed tetraalkylleads/TiCl4 was determined; Me>Et.i-Pr?n-Bu.

Asymmetric Synthesis of Optically Active Alcohols with Two Chiral Centres from a Racemic Aldehyde by the Selective Addition of Dialkylzinc Reagents Using Chiral Catalysts

Optically active alcohols with two chiral centres have been obtained in good to high e.e.s (enantiomeric excesses) from racemic 2-phenylpropanal 1 by diastereo- and enantio-selective addition of dialkylzinc reagents using (1S,2R)-(-)-N,N-dibutylnorephedrine (DBNE) and (S)-(+)-diphenyl(1-methyl-pyrrolidin-2-yl)methanol (DPMPM) as chiral catalysts.It was found that in the presence of (1S,2R)-(-)-DBNE, dialkylzinc selectively attacked racemic 1 from the Si-face of the aldehyde 1 regardless of the configuaration of 1 and that (S)-1 reacted faster with dialkylzinc than did (R)-1.

Highly Diastereoselective 1,2-Asymmetric Addition of Dialkylzincs to Chiral 2-Phenylpropanal Catalyzed by Amino Alcohol

Diastereoselective addition of dialkylzinc reagents to 2-phenylpropanal using amino alcohol as catalyst afforded erythro alcohols (Cram-selectivity) in high diastereomeric excess (up to 88percent d.e.).

Asymmetric Synthesis of Alcohols with Two Chiral Centres from a Racemic Aldehyde by the Selective Addition of Dialkylzinc Reagents using (1S,2R)-(-)-N,N-Dibutylnorephedrine and (S)-(+)-Diphenyl-(1-methylpyrrolidin-2-yl)methanol as Chiral Catalysts

Optically active alcohols with two chiral centers were obtained in up to 93percent enantiomeric excess by the selective addition of dialkylzinc reagents to the racemic aldehyde, 2-phenylpropanal, using the title compounds as chiral catalysts.

Kinetic Resolution of Racemic Aldehydes by Enantioselective Alkylation

Kinetic resolution of racemic aldehydes proceeds by enantioselective ethylation catalyzed by chiral β-aminoalcohols, thus providing a convenient method for the preparation of chiral aldehydes.