Stereoselective Monoamine Oxidase‐Catalyzed Oxidative Aza‐Friedel–Crafts Reactions of meso‐Pyrrolidines in Aqueous Buffer. Issue 10 (13th April 2016)

• Record Type: Journal Article
• Authors: de Graaff, Corien; Oppelaar, Barry; Péruch, Olivier; Vande Velde, Christophe M. L.; Bechi, Beatrice; Turner, Nicholas J.; Ruijter, Eelco; Orru, Romano V. A.
• Is Part Of: Advanced synthesis & catalysis. Volume 358:Issue 10(2016)
• Page Start: 1555
• Page End: 1560
• Publication Date: 2016-04-13
• Subjects: biocatalysis -- chemoenzymatic process -- oxidation -- 2‐pyrrolidines -- sustainable chemistry; Catalysis -- Periodicals; Organic compounds -- Synthesis -- Periodicals; Chemistry -- Periodicals; Chemistry, Technical -- Periodicals; Chemistry -- Periodicals; Catalysis -- Periodicals; Technology, Pharmaceutical -- Periodicals; 547.2
• DOI: 10.1002/adsc.201600038
• Languages: English
• ISSNs: 1615-4150

Abstract

Abstract: We disclose the highly diastereoselective combination of monoamine oxidase‐catalyzed oxidation of meso ‐pyrrolidines and aza‐Friedel–Crafts reactions in aqueous buffer to give valuable enantioenriched 2‐substituted pyrrolidines in a formal double CH activation process. A range of secondary as well as tertiary amines were shown to be suitable substrates for the biocatalytic oxidation and subsequent addition of a variety of C‐nucleophiles. Abstract :