Relay Catalysis: Enantioselective Synthesis of Cyclic Benzo-Fused Homoallylic Alcohols by Chiral Brønsted Acid-Catalyzed Allylboration/Ring Closing Metathesis

2013 ◽  
Vol 355 (6) ◽  
pp. 1058-1064 ◽  
Author(s):  
Santos Fustero ◽  
Elsa Rodríguez ◽  
Rubén Lázaro ◽  
Lidia Herrera ◽  
Silvia Catalán ◽  
...  
Keyword(s):  
Enantioselective Synthesis ◽  
Bronsted Acid ◽  
Brønsted Acid ◽  
Ring Closing Metathesis ◽  
Homoallylic Alcohols ◽  
Brönsted Acid ◽  
Acid Catalyzed ◽  
Chiral Bronsted Acid

scholarly journals Recent Developments and Applications of the Chiral Brønsted Acid Catalyzed Allylboration of Carbonyl Compounds

Synthesis ◽  
2018 ◽  
Vol 50 (10) ◽  
pp. 1935-1957 ◽  
Author(s):  
Daniel Sedgwick ◽  
Matthew Grayson ◽  
Santos Fustero ◽  
Pablo Barrio
Keyword(s):  
Carbonyl Compounds ◽  
Bronsted Acid ◽  
Brønsted Acid ◽  
The Past ◽  
Homoallylic Alcohols ◽  
Brönsted Acid ◽  
Recent Developments ◽  
Acid Catalyzed ◽  
Catalytic Asymmetric ◽  
Chiral Bronsted Acid

The 50-year-old allylboration reaction has seen dramatic developments since the dawn of the new century after the first catalytic asymmetric versions came into play. In the past decade alone, several methodologies capable of achieving the desired homoallylic alcohols in over 90% ee have been developed. This review focuses on the chiral Brønsted acid catalyzed allylboration reaction, covering everything from the very first examples and precedents to modern day variations and applications.1 Introduction2 Early Developments3 Synthetic Applications4 Variants5 Computational Contribution6 Conclusions

scholarly journals Chiral Brønsted acid-catalyzed Friedel–Crafts alkylation of electron-rich arenes with in situ-generated ortho-quinone methides: highly enantioselective synthesis of diarylindolylmethanes and triarylmethanes

2015 ◽  
Vol 51 (8) ◽  
pp. 1461-1464 ◽  
Author(s):  
Satyajit Saha ◽  
Santosh Kumar Alamsetti ◽  
Christoph Schneider
Keyword(s):  
Enantioselective Synthesis ◽  
Bronsted Acid ◽  
Brønsted Acid ◽  
Quinone Methides ◽  
Reaction Conditions ◽  
Brönsted Acid ◽  
Acid Catalyzed ◽  
Chiral Bronsted Acid ◽  
Hydrogen Bonded

Hydrogen-bonded, in situ-generated ortho-quinone methides undergo highly enantioselective Friedel–Crafts reactions with indoles and naphthols under mild reaction conditions.

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