Construction of Chiral Quaternary Carbon Centers by Catalytic Enantioselective Radical-Mediated Allylation of α-Iodolactones Using Allyltributyltin in the Presence of a Chiral Lewis Acid

1997 ◽  
Vol 119 (48) ◽  
pp. 11713-11714 ◽  
Author(s):  
Masatoshi Murakata ◽  
Toshiaki Jono ◽  
Yusuke Mizuno ◽  
Osamu Hoshino
Keyword(s):  
Lewis Acid ◽  
Quaternary Carbon ◽  
Carbon Centers ◽  
Chiral Lewis Acid

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.

Asymmetric synthesis of isoquinuclidines by Diels–Alder reaction of 1,2-dihydropyridine utilizing a chiral Lewis acid catalyst

Tetrahedron ◽  
2012 ◽  
Vol 68 (6) ◽  
pp. 1774-1781 ◽  
Author(s):  
Chigusa Seki ◽  
Masafumi Hirama ◽  
N.D.M. Romauli Hutabarat ◽  
Junko Takada ◽  
Chonticha Suttibut ◽  
...  
Keyword(s):  
Asymmetric Synthesis ◽  
Lewis Acid ◽  
Acid Catalyst ◽  
Alder Reaction ◽  
Diels Alder ◽  
Diels Alder Reaction ◽  
Chiral Lewis Acid ◽  
Lewis Acid Catalyst
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