124931-82-4

Upstream product

• 104-01-8 4-Methoxyphenylacetic acid 
• 18531-99-2 (S)-[1,1']-binaphthalenyl-2,2'-diol 

Downstream Products

• 55332-36-0 (S)-2-(4-methoxyphenyl)-3-methylbutyric acid 
• 124931-94-8 (R)-2-(4-Methoxy-phenyl)-propionic acid 2'-hydroxy-[1,1']binaphthalenyl-2-yl ester 
• 124931-94-8 (S)-2-(4-Methoxy-phenyl)-propionic acid 2'-hydroxy-[1,1']binaphthalenyl-2-yl ester 
• 124931-98-2 (R)-2-(4-Methoxy-phenyl)-4-methyl-pentanoic acid 2'-hydroxy-[1,1']binaphthalenyl-2-yl ester 

Relevant academic research and scientific papers

Synthesis of (+)- and (-)-ferruginol via asymmetric cyclization of a polyene

Stereoselectivity of modified polyenes which have a terminal benzene ring was found to be dependent on the size of substituent on the adjacent asymmetric carbon to the terminal benzene ring of the polyenes. (R)-(+)-2′-Hydroxy-1,1′-binaphthyl-2-yl(2R)-2-(4-methoxyphenyl)-5,9- dimethyldeca-4,8-dienoate gave(R)-(+)-2′-hydroxy-1,1′-binaphthyl-2-yl (4aS,9 R, 10aS)-1,2,3,4,4a,9,10,10a-octahydro-6-methoxy-1,1,4a-trimethylphenanthene-9- carboxylate stereoselectively by treatment with BF3-Et2O in nitromethane. The products were elaborated to (+)-ferruginol 1. (-)-Ferruginol 2 and (±)-ferruginol 3 were also synthesized via a similar synthetic route. The Royal Society of Chemistry 2000.

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.