92572-62-8Relevant academic research and scientific papers
Addition reactions of aldehydes to lithium enolates of 1,3-dioxolan-4-ones: A configurational reassessment
Battaglia, Arturo,Barbaro, Gaetano,Giorgianni, Patrizia,Guerrini, Andrea,Bertucci, Carlo,Geremia, Silvano
, p. 3551 - 3557 (2007/10/03)
The results for the addition reactions of chiral lithium (2S)-enolates of 1,3-dioxolan-4-ones to aldehydes and to acetophenone, yielding the corresponding dioxolanone alcohols have been revised. The results reported herein differ from those reported in th
α-ALKYLATION OF α-HETEROSUBSTITUTED CARBOXYLIC ACIDS WITHOUT RACEMIZATION; EPC-SYNTHESES OF TERTIARY ALCOHOLS AND THIOLS
Seebach, Dieter,Naef, Reto,Calderari, Giorgio
, p. 1313 - 1324 (2007/10/02)
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).
