Lewis Acid-Promoted Rearrangement of 2,3-Epoxy Alcohol Derivatives:  Stereochemical Control and Selective Formation of Two Types of Chiral Quaternary Carbon Centers from the Single Carbon Skeleton

2006 ◽  
Vol 71 (14) ◽  
pp. 5191-5197 ◽  
Author(s):  
Yasuyuki Kita ◽  
Satoshi Matsuda ◽  
Ryoko Inoguchi ◽  
Jnaneshwara K. Ganesh ◽  
Hiromichi Fujioka
Keyword(s):  
Lewis Acid ◽  
Carbon Skeleton ◽  
Quaternary Carbon ◽  
Carbon Centers ◽  
Epoxy Alcohol ◽  
Stereochemical Control ◽  
Selective Formation

scholarly journals Synergistic Brønsted/Lewis Acid Catalyzed Aromatic Alkylation with Unactivated Tertiary Alcohols or Di-tert-Butylperoxide to Synthesize Quaternary Carbon Centers

2021 ◽  
Author(s):  
Aaron Pan ◽  
Maja Chojnacka ◽  
Robert Crowley ◽  
Lucas Gottemann ◽  
Brandon Haines ◽  
...  
Keyword(s):  
Dft Calculations ◽  
Lewis Acid ◽  
Acid Catalysis ◽  
Alkylating Agents ◽  
Environmentally Benign ◽  
Quaternary Carbon ◽  
Tertiary Alcohols ◽  
Carbon Centers ◽  
Acid Catalyzed ◽  
Site Selective

Dual Brønsted/Lewis acid catalysis involving environmentally benign, readily accessible protic acid and iron promotes site-selective tert-butylation of electron-rich arenes using di-tert-butylperoxide. This transformation inspired the development of a synergistic Brønsted/Lewis acid catalyzed aromatic alkylation that fills a gap in the Friedel–Crafts reaction literature by employing unactivated tertiary alcohols as alkylating agents, leading to new quaternary carbon centers. Corroborated by DFT calculations, the Lewis acid serves a role in enhancing the acidity of the Brønsted acid. The use of non-allylic, non-benzylic, and non-propargylic tertiary alcohols represents an underexplored area in Friedel–Crafts reactivity.

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