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Enantioselective Synthesis of β‐Methyl Amines via Iridium‐Catalyzed Asymmetric Hydrogenation of N ‐Sulfonyl Allyl Amines
Author(s) -
Cabré Albert,
Verdaguer Xavier,
Riera Antoni
Publication year - 2019
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.201900748
Subject(s) - iridium , chemistry , enantioselective synthesis , isomerization , sulfonyl , catalysis , organic chemistry , asymmetric hydrogenation , combinatorial chemistry , medicinal chemistry , alkyl
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.