41718-40-5

Upstream product

• 109-65-9 1-bromo-butane 
• 101-97-3 Ethyl 2-phenylethanoate 
• 109-72-8 n-butyllithium 
• 132353-62-9 Phenyl-acetic acid 2'-methyl-[1,1']binaphthalenyl-2-yl ester 
• 74-88-4 methyl iodide 
• 132353-61-8 Phenyl-acetic acid 2'-methoxy-[1,1']binaphthalenyl-2-yl ester 
• 103-82-2 phenylacetic acid 
• 103-80-0 phenylacetyl chloride 
• 502-56-7 nonanone-5 
• 1589-82-8 phenylmagnesium bromide 
• 623-93-8 5-nonanol 
• 299899-85-7 nonan-5-yl methanesulfonate 

Downstream Products

• 25870-62-6 1-phenyl-2-hexanone 

Relevant academic research and scientific papers

Sulfonium ion-promoted traceless Schmidt reaction of alkyl azides

Schmidt reaction by sulfonium ions is described. General primary, secondary, and tertiary alkyl azides were converted to the corresponding carbonyl or imine compounds without any trace of the activators. This bond scission reaction through 1,2-migration of C-H and C-C bonds was accessible to the one-pot substitution reaction.

1,1′-binaphthalene-2,2′-diol as a chiral auxiliary. Diastereoselective alkylation of binaphthyl esters, complex-induced proximity effects in enolate formation, and one-step synthesis of an optically active β-substituted ketone

Diastereoselective alkylation of enolates derived from (S)-naphthyl phenylacetate 1 with LDA in THF gave the S,S-isomer as a major product. The diastereoselectivity increased as the bulkiness of the alkylating agent was increased. The low diastereomeric excess (～70%) of methylation was markedly raised to 92% by the use of n-BuLi as a base due to the complex-induced proximity effect (CIPE) in enolate formation. This highly diastereoselective methylation was used to synthesize the clinically important anti-inflammatory drugs (S)-naproxen (60) and (S)-suprofen (68). The stereochemistry of ketene trimethylsilyl acetals generated from several phenylacetates was investigated to understand the origin of the diastereoselectivity in this alkylation. Methyl phenylacetate (46) predominantly gave a (Z)-enolate by kinetic deprotonation, while the (E)-enolate was predominantly obtained from phenyl phenylacetate (47). An optically active ketone (88) was synthesized from binaphthyl ester 84 by a one-pot procedure involving the 1,4-addition, followed by the 1,2-addition, of organometallics. The CIPE again played a crucial role in the high enantiomeric excess in this case.

Complex-induced proximity effects in enolate formation. Highly diastereoselective α-methylation of binaphthyl esters of arylacetic acids

Highly diastereoselective methylation of binaphthyl esters of arylacetic acids and its application to the syntheses of antiinflammatory drugs, (S)-suprofen and (S)-naproxen.