Editorial: Smart use of metal reagents unlocks greener organic synthesis

2021 ◽  
pp. 100551
Author(s):  
Dmitry A. Valyaev
Keyword(s):  
Organic Synthesis ◽  
Metal Reagents

New preparative methods for allylic boronates and their application in stereoselective catalytic allylborations

2008 ◽  
Vol 80 (5) ◽  
pp. 913-927 ◽  
Author(s):  
Dennis G. Hall
Keyword(s):  
Organic Synthesis ◽  
Lewis Acid ◽  
Carbonyl Compounds ◽  
Bronsted Acid ◽  
Ring Systems ◽  
Brönsted Acid ◽  
Acid Catalyzed ◽  
Mechanistic Investigations ◽  
Carbonyl Allylation ◽  
Metal Reagents

Stereocontrolled additions of allylic metal reagents to carbonyl compounds constitute one of the most useful classes of transformations in organic synthesis. The recent development of Lewis and Brønsted acid-catalyzed manifolds for the allylboration of carbonyl compounds has opened doors toward an ideal carbonyl allylation methodology using stable and nontoxic allylic boronates as reagents. This paper describes the development of acid-catalyzed allylborations, mechanistic investigations of these new processes, and ongoing efforts toward general catalytic enantioselective allylboration methodologies. The preparation of optically enriched α-substituted allylic boronate reagents is discussed, as well as their applications in Lewis acid-catalyzed additions to afford skeletally diverse products like propionate units, polysubstituted furans, vinylcyclopropanes, and larger ring systems.

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