6695-22-3Relevant academic research and scientific papers
Chemistry of mucohalic acids; Part 6. A convenient synthesis of (Z)-α,β-dihaloacrolein
Duczek,Jahnisch
, p. 935 - 936 (1992)
(Z)-2,3-Dihalopropenals 2a,b have been prepared by decarboxylation of mucohalic acids [(Z)-2,3-dihalo-4-oxo-2-butenoic acids] 1 a,b.
Novel resolution process for racemic spiro-hydantoins
-
, (2008/06/13)
A novel three-step process for resolving a racemic spiro-hydantoin compound into its optical antipodes is disclosed, which involves (1) reacting said racemic compound with an optically-active asymmetric isocyanate of the formula RNCO, wherein R is (S)- or (R)-1-phenylethyl or (S) or (R)-1-(1-naphthyl)ethyl, to form the corresponding diastereomeric uredio compound; (2) separating the resulting diastereomeric mixture into its component parts, and (3) thereafter converting the separated ureido diastereomers obtained in step (b) to the corresponding asymmetric hydantoin compounds by treatment with an alkali metal lower alkoxide (C1 -C4), followed by acidification, whereupon the desired optical isomer is obtained. The final products so obtained, such as (4S)-(+)-6-fluoro-2,3-dihydro-spiro[4H-1-benzopyran-4,4'-imidazolidine]-2', 5'-dione (sorbinil) and (5'S)-3'-chloro-5', 6', 7', 8'-tetra-hydro-spiro[imidazolidine-4,5'-quinoline]-2,5-dione, are known to be useful in preventing or alleviating certain chronic diabetic complications. The aforementioned diastereomeric uredio intermediates are novel compounds.
