Enantioselective Synthesis of β‐Methyl Amines via Iridium‐Catalyzed Asymmetric Hydrogenation of N‐Sulfonyl Allyl Amines. Issue 18 (5th August 2019)

• Record Type: Journal Article
• Authors: Cabré, Albert; Verdaguer, Xavier; Riera, Antoni
• Is Part Of: Advanced synthesis & catalysis. Volume 361:Issue 18(2019)
• Page Start: 4196
• Page End: 4200
• Publication Date: 2019-08-05
• Subjects: iridium complexes -- asymmetric catalysis -- hydrogenation -- β-alkyl amines -- Drug synthesis -- Chiral P, N-ligands; Catalysis -- Periodicals; Organic compounds -- Synthesis -- Periodicals; Chemistry -- Periodicals; Chemistry, Technical -- Periodicals; Chemistry -- Periodicals; Catalysis -- Periodicals; Technology, Pharmaceutical -- Periodicals; 547.2
• DOI: 10.1002/adsc.201900748
• Languages: English
• ISSNs: 1615-4150

Abstract

Abstract: The iridium‐catalyzed asymmetric hydrogenation of several N ‐sulfonyl allyl amines is reported. All substrates can be easily obtained by the Ir‐catalyzed isomerization of N ‐tosylaziridines reported previously. The commercially available threonine‐derived phosphinite (UbaPHOX) iridium complex has been found to be the best catalyst for this catalytic application, affording β‐methyl amines with good to excellent ee values (up to 94%). The synthetic potential of this novel methodology was demonstrated by the formal synthesis of Lorcaserin and LY‐404187. Abstract :