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Paper | Regular issue | Vol 32, No. 10, 1991, pp.1969-1972
Published online, 1st January, 1970
DOI: 10.3987/COM-91-5828
Chiral Prodyes: Synthesis and Full Characterization of (S)-1-Phenylethylamides of the Optically Active O-Methyldihydrofluoresceins

Malgorzata Brzostowska, Arnold Brossi,* and Judith L. Flippon. Anderson

*Laboratory for the Structural Biology, NIDDK, National Instutute of Health, Bethesda, MD 20892-0815, U.S.A.

Abstract

O-Dihydrofluorescein (3) on reaction with (S)-(—)-1-phenylethylamine afforded aminde (5) as a mixture of diastereomers which resisted chromatographic separation. The mixture of amides (6) and (7), however, obtained from 5 by catalytic hydrogenation could be separated by hplc. The X-ray analysis of amide (6) showed that it has the (9S)-absolute configuration. This result attests that it is possible to obtain dihydrofluoresceins with differently substituted benzene rings in the form of enantiomers.