648433-02-7

Upstream product

• 6118-51-0 exo-3,6-epoxy-1,2,3,6-tetrahydrophthalic anhydride 
• 100-51-6 benzyl alcohol 

Downstream Products

• 936735-61-4 C₁₆H₁₆O₅ 
• 844865-37-8 (1S,2S,3S,4R)-3-[Benzyl-((R)-1-benzylcarbamoyl-3-methyl-butyl)-amino]-7-oxa-bicyclo[2.2.1]hept-5-ene-2-carboxylic acid methyl ester 

Relevant academic research and scientific papers

A chiral bifunctional sulfonamide as an organocatalyst: Alcoholysis of σ-symmetric cyclic dicarboxylic anhydrides

Enantioselective alcoholysis of σ-symmetric cyclic dicarboxylic anhydrides with benzyl alcohol catalyzed by a chiral bifunctional sulfonamide was achieved in up to 98% ee at 5 mol% loading. Georg Thieme Verlag Stuttgart - New York.

A novel highly selective chiral auxiliary for the asymmetric synthesis of L- and D-α-amino acid derivatives via a multicomponent ugi reaction

(Chemical Equation Presented) This paper describes the synthesis of a bicyclic β-amino acid scaffold in both pure enantiomeric forms and its application as chiral auxiliary in an intramolecular version of the Ugi multicomponent reaction (U-5C-4CR) to prepare α-amino acid derivatives of both D- and L-series in a straightforward and very stereoselective manner. The mild conditions required for the Ugi condensation and for the removal of the chiral auxiliary make this method very attractive to prepare a wide range of differently structured N-alkylated and unalkylated amino acid derivatives.

An alkaloid-mediated desymmetrization of meso-anhydrides via a nucleophilic ring opening with benzyl alcohol and its application in the synthesis of highly enantiomerically enriched β-amino acids

The cinchona alkaloid-mediated opening of prochiral cyclic anhydrides in the presence of benzyl alcohol leading to optically active hemiesters is described. Structurally diverse anhydrides are converted into their corresponding benzyl monoesters with either enantiomer being obtained with up to 99 percent e.e. by using quinine or quinidine as the directing additive. A simple aqueous work-up protocol permits the isolation of the products in analytically pure form and the recovery of the alkaloids almost quantitatively. These hemiesters can be converted to N-protected β-amino esters by means of Curtius degradation of the corresponding acyl azides. Subsequent cleavage of both protecting groups by a single reaction step leads to the free β-amino acids in excellent yields. The efficiency of this procedure is demonstrated by the short asymmetric synthesis of the fungicide cis-pentacin delivering the amino acid with >99.7 percent enantiomeric excess.