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- Title
Iridium‐Catalyzed Asymmetric Allylic Aromatization Reaction.
- Authors
Liu, Xi‐Jia; Zheng, Chao; Yang, Yi‐Han; Jin, Shicheng; You, Shu‐Li
- Abstract
Described herein is an asymmetric allylic aromatization (AAAr) strategy that employs readily accessible equivalents of benzylic nucleophiles in iridium‐catalyzed allylic substitution reactions with the concomitant formation of aromatic rings by aromatization. The optimized reaction conditions involving a catalyst derived from a commercially available iridium precursor and the Carreira ligand are compatible with equivalents of benzylic nucleophiles derived from 4‐ or 5‐methyloxazoles, 5‐methylthiazoles, 4‐ or 5‐methylfurans, 2‐ or 3‐methylbenzofurans, 3‐methylbenzothiophene, 3‐methylindole, 1‐methylnaphthalene, and methylbenzene. This strategy provides straightforward accesses to valuable heterocyclic aromatic compounds, bearing a homobenzylic stereogenic center, in an enantiopure form and would be difficult to access otherwise. The versatility of the reaction was showcased by the further elaboration of the products into useful building blocks and a drug analogue.
- Subjects
AROMATIZATION; SUBSTITUTION reactions; HETEROCYCLIC compounds; AROMATIC compounds; NUCLEOPHILES; ALLYLIC amination
- Publication
Angewandte Chemie, 2019, Vol 131, Issue 31, p10603
- ISSN
0044-8249
- Publication type
Article
- DOI
10.1002/ange.201904156