ChemInform Abstract: X=Y-ZH Systems as Potential 1,3-Dipoles. Part 40. Chiral Azomethine Ylides from Homochiral Cyclic α-Amino Esters. Unusual Regiospecific Deprotonation of Iminium Ions.

ChemInform ◽  
2010 ◽  
Vol 25 (2) ◽  
pp. no-no
Author(s):  
R. GRIGG ◽  
Z. RANKOVIC ◽  
M. THORNTON-PETT ◽  
A. SOMASUNDERAM
Keyword(s):  
Azomethine Ylides ◽  
Amino Esters ◽  
Iminium Ions

Aminoboranes as new iminium ion generators in amination reactions

2006 ◽  
Vol 78 (7) ◽  
pp. 1377-1387 ◽  
Author(s):  
Michinori Suginome
Keyword(s):  
Reductive Amination ◽  
Carbonyl Carbon Atom ◽  
Amino Groups ◽  
Boron Compounds ◽  
Enol Ethers ◽  
Silyl Enol Ethers ◽  
Amino Esters ◽  
Iminium Ions ◽  
Iminium Ion ◽  
Silyl Acetals

The utilization of aminoborane derivatives in amination reactions such as Strecker-type aminative cyanation, Mannich-type reaction, and reductive amination is described. Bis(dialkylamino)cyanoboranes and bis(dialkylamino)boron enolates underwent the concurrent transfer of the amino group and either the cyano or the enoxy group from the boron to carbonyl carbon atom in their reaction with aldehydes, leading to the formation of α-amino nitriles and β-amino ketones, respectively. Bis(dialkylamino)borane derivatives that lack the additional nucleophilic groups on the boron atoms were found to serve as effective generators of iminium ions from aldehydes. In the presence of these aminoboranes, reactions of aldehydes with ketene silyl acetals or silyl enol ethers take place, giving Mannich-type products, i.e., β-amino esters and ketones, selectively. Using diisopropylamino-substituted boron compounds, which are designed as "universal" iminium ion generators, reactions of free sec-amines, aldehydes, and ketene silyl acetals proceed efficiently, giving β-amino esters in which the amino groups are derived exclusively from the free amines. The use of the universal iminium ion generator is also effective for reductive amination of aldehydes, in which NaBH4 is used as a hydride donor.

Stereoselective 1,3-Dipolar Cycloaddition of a Maleate Derivative with Azomethine Ylides Derived from α-Amino Esters: Synthesis of 3-Pyrrolines

Synlett ◽  
2007 ◽  
Vol 2007 (08) ◽  
pp. 1284-1288
Author(s):  
Sandrine Deloisy ◽  
Adrien Soret ◽  
Régis Guillot ◽  
Gérard Rousseau ◽  
Luis Blanco
Keyword(s):  
Azomethine Ylides ◽  
Dipolar Cycloaddition ◽  
Amino Esters

ChemInform Abstract: Kinetic Acidity of Iminium Ions. 2-Alkynyl- and 2,5-Dialkynyl-pyrrolidines via the Iminium Ion Route to Azomethine Ylides.

ChemInform ◽  
2010 ◽  
Vol 33 (33) ◽  
pp. no-no
Author(s):  
Ronald Grigg ◽  
Visuvanathar Sridharan ◽  
Mark Thornton-Pett ◽  
Jun Wang ◽  
Juan Xu ◽  
...  
Keyword(s):  
Azomethine Ylides ◽  
Kinetic Acidity ◽  
Iminium Ions ◽  
Iminium Ion

Stereoselective 1,3-Dipolar Cycloaddition of a Maleate Derivative with Azomethine Ylides Derived from α-Amino Esters: Synthesis of 3-Pyrrolines.

ChemInform ◽  
2007 ◽  
Vol 38 (38) ◽  
Author(s):  
Adrien Soret ◽  
Regis Guillot ◽  
Gerard Rousseau ◽  
Luis Blanco ◽  
Sandrine Deloisy
Keyword(s):  
Azomethine Ylides ◽  
Dipolar Cycloaddition ◽  
Amino Esters

scholarly journals Simple Generation of Ester-Stabilized Azomethine Ylides from 2-Amino Esters and Carbonyl Compounds. Stereochemistry of Their Cycloadditions

1987 ◽  
Vol 60 (11) ◽  
pp. 4067-4078 ◽  
Author(s):  
Otohiko Tsuge ◽  
Shuji Kanemasa ◽  
Masayuki Ohe ◽  
Kiyotaka Yorozu ◽  
Shigeori Takenaka ◽  
...  
Keyword(s):  
Carbonyl Compounds ◽  
Azomethine Ylides ◽  
Amino Esters ◽  
Stabilized Azomethine Ylides
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