63828-75-1

Upstream product

• 2362-61-0 trans-2-Phenylcyclohexanol 
• 98-88-4 benzoyl chloride 
• 65-85-0 benzoic acid 
• 4998-93-0 2,2,2-tribromoethyl benzoate 
• 618-32-6 Benzoyl bromide 
• 2362-61-0 cis-2-phenylcyclohexanol 
• 93-97-0 benzoic acid anhydride 
• 98919-68-7 (1R,2S)-trans-2-phenylcyclohexanol 

Relevant academic research and scientific papers

(S)-proline-derived catalysts for the acylative kinetic resolution of alcohols: A remote structural change allows a complete selectivity switch

A systematic preliminary study has identified a suite of catalysts, all readily prepared and derived from (S)-proline, which differ by a remote substituent only. If this substituent is capable of hydrogen-bond donation the catalyst will promote the resolu

Efficient method for the preparation of carboxylic acid alkyl esters or alkyl phenyl ethers by a new-type of oxidation-reduction condensation using 2,6-dimethyl-1,4-benzoquinone and alkoxydiphenylphosphines

A new-type of oxidation-reduction condensation proceeded smoothly to afford carboxylic acid alkyl esters or alkyl phenyl ethers in good to high yields by combined use of alkoxydiphenylphosphines (1) having primary, bulky secondary or tertiary alkoxy groups, a mild quinone-type oxidant such as 2,6-dimethyl-1,4-benzoquinone (DMBQ) and carboxylic acids or phenols. Generally, alkoxydiphenylphosphines were prepared easily from chlorodiphenylphosphine (2) and alcohols in the presence of pyridine, and were isolated by distillation. On the other hand, the phosphines 1 were also prepared in situ from N,N-dimethylaminodiphenylphosphine (3a) and primary or secondary alcohols while primary, bulky secondary or tertiary alkoxydiphenylphosphines were alternatively formed in situ by adding 2 to the "BuLi-treated alcohols in order to perform the above reactions by a one-pot procedure from alcohols and nucleophiles. The reaction of thus formed 1, DMBQ and carboxylic acids or phenols afforded the corresponding alkylated products, including hindered secondary and tertiary alkylated ones, in good to high yields at room temperature. In the case of using chiral secondary alcohols, the corresponding carboxylic acid alkyl esters were obtained as well in high yields with perfect inversion of stereochemistry by SN2 replacement.

Preparation of various carboxylic acid esters from bulky alcohols and carboxylic acids by a new type oxidation-reduction condensation using 2,6-dimethyl-1,4-benzoquinone

A new-type oxidation-reduction condensation by using 2,6-dimethyl-1,4-benzoquinone (DMBQ), carboxylic acids and in situ formed alkoxydiphenylphosphines (1) including the bulky alkoxy group-substituted ones proceeded smoothly to afford the corresponding carboxylic acid esters in good to high yields. Alkoxydiphenylphosphines were formed in situ by treating either N,N-dimethylaminodiphenylphosphine (Ph2PNMe2) with primary or secondary alcohols or chlorodiphenylphosphine with the lithium salts of primary, secondary and tertiary alcohols.

A polymer-supported proline-based diamine catalyst for the kinetic resolution of racemic secondary alcohols

The preparation of polymer-supported proline-based diamine catalyst 12 for the kinetic resolution of racemic mixtures of secondary alcohols is described. Not only is the catalyst effective for the resolution of a host of different alcohols, it can also be recovered and reused several times without loss of either activity or selectivity. The catalyst has been used in conjunction with a polymer-supported sequestration strategy, giving rise to an essentially pure mixture of resolved products that can be separated using flash chromatography.

Direct transacylation of 2,2,2-trihaloethyl esters with amines and alcohols using phosphorus(III) reagents for reductive fragmentation and in situ activation

Amides and esters have been synthesized from 2,2,2-trihaloethyl esters in one pot using phosphorus(III) reagents as reductants, with resultant carboxylate activation as an acyloxyphosphonium intermediate, and in situ trapping by amine or alcohol nucleophiles. Secondary and tertiary amides were synthesized, including a dipeptide, in good yields using hexamethylphosphorous triamide, (Me2N)3P, as reducing agent. Optimal yields of esters derived from primary and secondary alcohols were obtained using tributylphosphine and DMAP. Tribromoethyl esters provided yields superior to those obtained with trichloroethyl esters.

Catalytic asymmetric acylation of racemic secondary alcohols with benzoyl chloride in the presence of a chiral diamine

Nonenzymatic kinetic resolution of racemic secondary alcohols is an efficient synthetic method to obtain optically active compounds in organic chemistry. Catalytic asymmetric acylation of racemic secondary alcohols has been successfully performed with achiral benzoyl chloride in the presence of only 0.3 mol% of chiral diamine (3) derived from (S)-proline, combined with 0.5 equivalent of triethylamine. This asymmetric acylation of various racemic cyclic secondary alcohols, 5, 6, or 8 membered cycloalkanols (1a-1c), hydroxyesters (1d and 1e), and bromohydrins (1f and 1g) gave the corresponding optically active benzoates (84-97% ee) and unreacted alcohols (79-95% ee). Racemic acyclic secondary alcohols (1h-1j) were also acylated in moderate enantioselectivity.

Remarkably fast acylation of alcohols with benzoyl chloride promoted by TMEDA

Reaction of alcohols with benzoyl chloride in the presence of TMEDA at - 78°C resulted in very fast acylation to afford the corresponding benzoates in excellent yields.

Nonenzymatic enantioselective acylation of racemic secondary alcohols catalyzed by a SnX2-Chiral diamine complex

Kinetic resolution of racemic secondary alcohols has been achieved by the reaction with benzoyl halide in the presence of a SnX2-chiral diamine complex to afford the corresponding benzoate in good to excellent enantioselectivities.

Novel, Enantioselective Lactone Construction. First Synthesis of Methylenolactocin, Antitumor Antibiotic from Penicillium sp.

The first synthesis of (-)-methylenolactocin, which illustrates a novel approach to enantiopure γ-butyrolactones and serves to confirm the structure and establish the absolute stereochemistry of the natural product, is reported.