193214-06-1Relevant academic research and scientific papers
Highly selective chirally templated isomunchnone cycloadditions of achiral aldehydes: Synthesis of an enantiopure α,β-Dihydroxyacid
Drew, Michael G. B.,Fengler-Veith, Marion,Harwood, Laurence M.,Jahans, Archie W.
, p. 4521 - 4524 (2007/10/03)
Additions of p-nitro- and p-methoxybenzaldehyde to isomunchnone derivatives of (5S)-phenyloxazin-3-one and -2,3-dione led to corresponding adducts (3,4,6) with excellent diastereofacial and exo-selectivity. Hydrolysis and subsequent cleavage of adduct 3 permitted recovery of the original template and furnished dihydroxyacid 9 that was transformed into the known ethyl ester 10. Comparison of its optical rotation with the literature value confirmed its high optical purity.
