92572-47-9

Upstream product

• 92572-37-7 (2S,5S)-5-benzyl-2-(tert-butyl)-1,3-dioxolan-4-one 
• 106-95-6 allyl bromide 
• 556-56-9 allyl iodid 

Downstream Products

• 871711-57-8 (2S,5S)-5-benzyl-2-(tert-butyl)-5-(3-hydroxypropyl)-1,3-dioxolan-4-one 
• 103404-94-0 (+)-Homocitric acid lactone 
• 871711-58-9 (2S,5S)-5-benzyl-2-(tert-butyl)-5-(2-carboxyethyl)-1,3-dioxolan-4-one 

Relevant academic research and scientific papers

Asymmetric synthesis of (S)-homocitric acid lactone

Starting from (S)-phenylalanine, an asymmetric synthesis of (S)-homocitric acid lactone was achieved using Seebach's SRS methodology. An intermediate for the synthesis of the (S)-per-homocitric acid lactone has also been synthesized.

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).