A Practical Access to Highly Enantiomerically Pure Flavanones by Catalytic Asymmetric Transfer Hydrogenation

• Published in: Angewandte Chemie (International ed.) Vol. 52; no. 44; pp. 11651 - 11655
• Main Authors: Lemke, Marie-Kristin, Schwab, Pia, Fischer, Petra, Tischer, Sandra, Witt, Morris, Noehringer, Laurence, Rogachev, Victor, Jäger, Anne, Kataeva, Olga, Fröhlich, Roland, Metz, Peter
• Format: Journal Article
• Language: English
• Published: Weinheim WILEY-VCH Verlag 25.10.2013; WILEY‐VCH Verlag; Wiley; Wiley Subscription Services, Inc
• Edition: International ed. in English
• Subjects: asymmetric catalysis; Asymmetry; Biocompatibility; Biological Products; Catalysis; Catalysts; Chemistry; Chemistry, Multidisciplinary; Flavanones - chemistry; flavonoids; glabrol; Hydrogenation; Ketones; kinetic resolution; Molecular Structure; natural products; Physical Sciences; Reaction kinetics; Science & Technology; Stereoisomerism; Synthesis; ACYLTRANSFERASE; natural products; KETONES; ENANTIOSELECTIVE SYNTHESIS; kinetic resolution; EFFICIENT SYNTHESIS; asymmetric catalysis; glabrol; flavonoids; 8-PRENYLNARINGENIN; CHIRAL RHODIUM; CONSTITUENTS
• ISSN: 1433-7851; 1521-3773
• DOI: 10.1002/anie.201306500

A surprisingly selective, non‐enzymatic kinetic resolution of readily available, racemic β‐chiral ketones enabled the title process, which was applied to a rapid synthesis of several bioactive flavanones in virtually enantiopure form (see scheme; MOM=methoxymethyl, Ts=p‐toluenesulfonyl).