Iridium-Catalyzed Asymmetric Allylic Substitution of Methyl Azaarenes.
Angew Chem Int Ed Engl
; 61(20): e202200164, 2022 05 09.
Article
in En
| MEDLINE
| ID: mdl-35238122
ABSTRACT
Herein, an Ir-catalyzed asymmetric allylic substitution reaction of methyl azaarenes is described. Azaarenes such as (benzo)thiazole, oxazole, benzoimidazole, pyridine, and (iso)quinoline are all tolerated. The corresponding chiral azaarene derivatives are obtained in good yields with high enantioselectivity (up to 96 % yield and 99 % ee). The utilization of the Knochel reagent TMPZnBrâ
LiBr warrants the in situ formation of benzylic nucleophiles without additional activating reagents. 1 Hâ
NMR studies suggested a two-fold function of the Knochel reagent in this reaction. The synthetic utility of this method has been showcased by a concise enantioselective synthesis of an allosteric protein kinase modulator.
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Full text:
1
Collection:
01-internacional
Database:
MEDLINE
Main subject:
Iridium
Language:
En
Journal:
Angew Chem Int Ed Engl
Year:
2022
Document type:
Article
Affiliation country:
China