Regioselective synthesis of functionalized dihydroisoquinolines from o-alkynylarylaldimines via the Reformatsky reaction

2016 ◽  
Vol 14 (41) ◽  
pp. 9896-9906 ◽  
Author(s):  
Tohasib Yusub Chaudhari ◽  
Urvashi Urvashi ◽  
Sandeep K. Ginotra ◽  
Pooja Yadav ◽  
Gulshan Kumar ◽  
...  
Keyword(s):  
Lewis Acid ◽  
Regioselective Synthesis ◽  
Reformatsky Reaction ◽  
Novel Approach ◽  
The Reformatsky Reaction

A novel approach for the synthesis of functionalized 1,2-dihydroisoquinolines from o-alkynylarylaldimines via the Reformatsky reaction without the aid of an external Lewis acid has been described.

The Reformatsky Reaction with Benzalaniline

1943 ◽  
Vol 65 (11) ◽  
pp. 2255-2256 ◽  
Author(s):  
Henry Gilman ◽  
Merrill Speeter
Keyword(s):  
Reformatsky Reaction ◽  
The Reformatsky Reaction

A NEW MODIFICATION OF THE REFORMATSKY REACTION

1931 ◽  
Vol 53 (5) ◽  
pp. 1842-1846 ◽  
Author(s):  
J. A. Nieuwland ◽  
S. Florentine. Daly
Keyword(s):  
Reformatsky Reaction ◽  
The Reformatsky Reaction

STUDIES ON THE MECHANISMS OF CYCLIZATION OF RING A OF STEROIDS DURING THE REFORMATSKY REACTION

1958 ◽  
Vol 36 (9) ◽  
pp. 1260-1267
Author(s):  
R. D. H. Heard ◽  
G. A. Balla ◽  
J. R. Jamieson ◽  
P. Ziegler
Keyword(s):  
Methyl Ester ◽  
Acid Methyl Ester ◽  
Reformatsky Reaction ◽  
Acid Methyl ◽  
The Reformatsky Reaction

The Reformatsky reaction of 3,5-seco-5-ketocholestan-3-oic acid methyl ester with methyl bromoacetate yielded 2-carbohydroxycholestenone, cholestenone, and 4-carbomethoxycholestenone. The appearance of these products indicated that cyclization of ring A proceeded along two different paths; this conclusion was confirmed by the use of methyl bromoacetate-1-C14 and -2-C14.

First enantioselective one-pot, three-component imino Reformatsky reaction

2006 ◽  
Vol 78 (2) ◽  
pp. 287-291 ◽  
Author(s):  
Pier Giorgio Cozzi ◽  
Eleonora Rivalta
Keyword(s):  
Simple Procedure ◽  
Enantiomeric Excess ◽  
Multiple Roles ◽  
Reformatsky Reaction ◽  
One Pot ◽  
Bond Forming ◽  
Carbon Carbon Bond ◽  
Three Component Reaction ◽  
Hydroxy Esters ◽  
The Reformatsky Reaction

The Reformatsky reaction is the well-recognized carbon-carbon bond-forming reaction of α-halo esters with aldehydes or ketones in the presence of Zn metal to give β-hydroxy esters. Recently, it has been reported that Rh- and Ni-catalyzed Reformatsky reaction, in which R2Zn (R = Me, Et) acts as the Zn source, reacted smoothly with carbonyl compounds and imines. Taking advantage of N-methylephedrine as a cheap and recoverable chiral ligand, we have discovered the first homogeneous enantioselective Ni-catalyzed imino Reformatsky reaction. The process is a one-pot, three-component reaction, in which Me2Zn plays multiple roles as dehydrating agent, reductant, and coordinating metal. Broad scope, high enantiomeric excess, and a simple procedure are adding value to our findings.

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