313374-39-9

Upstream product

• 3262-89-3 triphenylboroxine 
• 557-20-0 diethylzinc 
• 1078-58-6 diphenylzinc 
• 925-90-6 ethylmagnesium bromide 
• 100-58-3 phenylmagnesium bromide 
• 7646-85-7 zinc(II) chloride 
• 109-72-8 n-butyllithium 
• 2633-75-2 ethylzinc chloride 
• 98-80-6 phenylboronic acid 

Downstream Products

• 99412-45-0 (S)-naphthalen-2-yl(phenyl)methanol 
• 1062517-51-4 (+)-(R)-trimethyl(3-phenylhept-1-yn-1-yl)silane 
• 1062518-31-3 (S)-trimethyl(3-phenylhept-1-yn-1-yl)silane 
• 1062518-26-6 (S)-pent-1-yne-1,3-diyldibenzene 
• 1062518-02-8 (R)-pent-1-yne-1,3-diyldibenzene 
• 113565-51-8 (R)-2-furylphenylmethanol 
• 4484-57-5 (S)-2-furyl(phenyl)methanol 
• 5583-33-5 (R)-(-)-α-phenyl-2-pyridylmethanol 
• 5583-33-5 (S)-(+)-α-phenyl-2-pyridylmethanol 
• 945-49-3 (S)-cyclohexylphenylmethanol 
• 945-49-3 (R)-cyclohexylphenylmethanol 
• 14898-86-3 (R)-2-methyl-1-phenylpropan-1-ol 
• 34857-28-8 (S)-2-methyl-1-phenylpropan-1-ol 
• 614-54-0 (R)-1-phenylheptanol 

Relevant academic research and scientific papers

Catalytic asymmetric 1,2-Addition/Lactonization tandem reactions for the syntheses of chiral 3-Substituted phthalides using organozinc reagents

Using chiral phosphoramide ligand 2d-Zn (II) complex derived from (1R,2R)-1,2-diphenylethylenediamine as the catalyst, we have developed efficient catalytic asymmetric 1,2-addition/lactonization tandem reactions of diverse organozinc reagents with varied methyl 2-formylbenzoates for the construction of optically enriched 3-aryl or alkyl substituted phthalides, which are significant building blocks of many important chiral pharmaceuticals and natural products. The corresponding products could be afforded with good to excellent yields (up to 95%) and moderate to good enantioselectivities (up to 89%).

Organo-zinc Promoted Diastereoselective C-Arylation of 1,2-Anhydrosugars from Arylboronic Acids

α-C-arylglycosides can be obtained through the addition of aryl zinc reagents to sugar epoxides. The required aryl zinc nucleophiles can be easily obtained from the corresponding boronic acids by B-Zn exchange and attack sugar 1,2 epoxides in a highly diastereoselective fashion to generate 1,2-cis-α-hexapyranosyl aryl glycosides under ligand- and base-free conditions.

Zn(salen)-catalyzed enantioselective phenyl transfer to aldehydes and ketones with organozinc reagent

Abstract A chiral zinc complex of salen was found to be an efficient catalyst for the phenyl transfer of organozinc reagent to aromatic aldehydes and ketones. High enantioselectivities were obtained in reactions of both aromatic aldehydes and ketones (up to 97% and 92% ee, respectively).

Diastereomeric aziridine carbinol catalyzed enantioselective arylation reaction: Toward the asymmetric synthesis of both enantiomers of chiral 3-aryl phthalide

The diastereomeric aziridine carbinols are applied, respectively, as efficient chiral ligand in the catalysis of asymmetric arylation and sequential arylation-lactonization cascade. The two diastereomers, which are facilely synthesized from the same chiral source, function as pseudo enantiomers in arylation of aromatic aldehydes providing the different enantiomers of the diarylmethanols with almost the same excellent enantioselectivities. The arylation method is also carried out in tandem with lactonization process to afford a concise synthetic approach to both enantiomers of optically active 3-aryl phthalide.

Practical catalytic asymmetric synthesis of diaryl-, aryl heteroaryl-, and diheteroarylmethanols

Enantioenriched diaryl-, aryl heteroaryl-, and diheteroarylmethanols exhibit important biological and medicinal properties. One-pot catalytic asymmetric syntheses of these compounds beginning from readily available aryl bromides are introduced. Thus, lith

METHODS FOR PREPARING DIORGANOZINC COMPOUNDS

There are provided methods for preparing the diorganozmc compounds of formula R2Zn (I or Ia), where R is a defined organic radical, and the two R groups can be the same or different The starting material is the zinc compound ZnX2 (II) or R2ZnX (IIa), where X is a defined anion and R2 is a defined organic radical. The zinc reagent of type II is combined with a Grignard reagent and also, when X is Cl or Br, with an alkali metal reagent (VI) to form the diorganozinc product (I or Ia). Also provided are methods for preparing the zinc alcoholates of formula Zn(OR1)2 by reaction of ZnX2, where X = Cl or Br, with an alkali metal reagent of the formula MOR1, where M = Na or K, and where R1 is a defined organic radical.

Practical implications of boron-to-zinc transmetalation for the catalytic asymmetric arylation of aldehydes

(Chemical Equation Presented) Faster than believed: Transmetalation from aryl boronic acids and triaryl boroxines to diethylzinc takes place within minutes following a two-step, low-energy pathway (see picture), according to density functional calculations and reaction microcalorimetry measurements. The experimental conditions for a practical, atom-economical, and highly enantioselective catalytic arylation of a variety of aldehydes have been developed from these data.