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Catalytic Approach to Diverse α‐Aminoboronic Acid Derivatives by Iridium‐Catalyzed Hydrogenation of Trifluoroborate‐Iminiums
Author(s) -
Šterman Andrej,
Košmrlj Janez,
Žigart Nina,
Gobec Stanislav,
Sosič Izidor,
Časar Zdenko
Publication year - 2021
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.202001350
Subject(s) - chemistry , iminium , iridium , catalysis , scope (computer science) , substrate (aquarium) , combinatorial chemistry , asymmetric hydrogenation , organic chemistry , enantioselective synthesis , computer science , oceanography , programming language , geology
A series of structurally diverse benzyl protected trifluoroborate‐ammoniums were prepared in good to high yields by an efficient hydrogenation of corresponding trifluoroborate‐iminiums using Crabtree's catalyst. Subsequent N ‐ and B ‐deprotections were demonstrated on selected examples to provide several α‐aminoboronic acids. Preliminary experiments on asymmetric version of the reaction indicated a correlation between E / Z ‐ratio in the trifluoroborate‐iminium substrate and enantioselectivity. The broad scope, operational simplicity and efficiency of the presented method imply its high potential for a facile access to libraries of α‐aminoboronic acid derivatives that can be used in medicinal chemistry applications and beyond.