92572-57-1

Upstream product

• 630-19-3 pivalaldehyde 
• 56209-56-4 2-((2S,4S)-2-(tert-butyl)-5-oxo-1,3-dioxolan-4-yl)acetic acid 
• 186906-71-8 2-((2R, 4R)-2-tert-butyl-5-oxo-1,3-dioxolan-4-yl) acetic acid 
• 100-39-0 benzyl bromide 

Downstream Products

• 909247-87-6 methyl ((2R,4R)-2-tert-butyl-4-benzyl-5-oxo-1,3-dioxolan-4-yl)carbamate 
• 26581-12-4 dimethyl (2R)-2-benzyl-2-hydroxysuccinate 
• 51692-94-5 (R)-2-benzyl-2-hydroxy-succinic acid 

Relevant academic research and scientific papers

A facile method for synthesis of (R)-(-)- and (S)-(+)-homocitric acid lactones and related α-hydroxy dicarboxylic acids from D- or L-malic acid

We report here a simple and convenient route for the stereoselective synthesis of (R)-(-)- and (S)-(+)-homocitric acid lactones, which play very important roles in biochemistry. The method involves only three steps, starting from the readily available met

A concise synthesis of (R)- and (S)-α-alkyl isoserines from d- and l-malic acids

A simple and diastereoselective method for the synthesis of (R)- and (S)-α-alkyl isoserines has been developed in four steps starting from commercially available d- and l-malic acid, respectively. This approach features stereocontrolled alkylation of 2-(2

Enantioselective synthesis of α-alkylmalates as the pharmacophoric group of several natural alkaloids and glycosides

A general enantioselective synthesis of α-alkylmalates found in Cephalotaxus and Orchidaceae species is described. This preparation is based upon Seebach's procedure for the alkylation of D-malic acid with self-regeneration of stereogenic centers. Reactio

α-ALKYLATION OF α-HETEROSUBSTITUTED CARBOXYLIC ACIDS WITHOUT RACEMIZATION; EPC-SYNTHESES OF TERTIARY ALCOHOLS AND THIOLS

α-Hydroxy- and α-mercapto-carboxylic acids are condensed with pivalaldehyde to give 2-t-butyl-5-substituted-1,3-dioxolanones or 1,3-oxathiolanones (2); the predominate cis-isomers are separeted by crystallization.The cis-disubstituted heterocycles 2 derived from lactic, mandelic and malic acid funish, after deprotonation with LDA, reaction with electrophiles such as alkyl halides, aldehydes and ketones, and hydrolysis α-branched α-hydroxy-carboxylic acids (3, 6, 8, 9, 10).These result from an overall substitution of the proton in the α-CO position with retention of configuration.The optically active carboxylic acids are α-alkylated without racemization and without employment of a chiral auxiliary ("self-reproduction of chirality", Scheme 1).The diastereoselectivities (ds) are generally >95percent (Table 1, 2, and 20-25).