Strecker Reaction: Catalytic Addition of Hydrogen Cyanide or Trimethylsilyl Cyanide to Ketimines

2012 ◽  
pp. 1
Author(s):  
K. Hof ◽  
K. M. Lippert ◽  
P. R. Schreiner
Keyword(s):  
Hydrogen Cyanide ◽  
Trimethylsilyl Cyanide ◽  
Strecker Reaction ◽  
Catalytic Addition

A Remarkable Titanium-Catalyzed Asymmetric Strecker Reaction using Hydrogen Cyanide at Room Temperature

2010 ◽  
Vol 352 (13) ◽  
pp. 2153-2158 ◽  
Author(s):  
Balamurugan Ramalingam ◽  
Abdul Majeed Seayad ◽  
Li Chuanzhao ◽  
Marc Garland ◽  
Kazuhiko Yoshinaga ◽  
...  
Keyword(s):  
Hydrogen Cyanide ◽  
Room Temperature ◽  
Strecker Reaction

Zur Synthese fluororganischer O-(Trimethylsilyl)-cyanhydrine / Synthesis of Fluoroorganic O-(Trimethylsilyl)Cyanhydrines

1998 ◽  
Vol 53 (3) ◽  
pp. 296-306 ◽  
Author(s):  
Michael Sander ◽  
Wolfgang Sundermeyer
Keyword(s):  
Carboxylic Acid ◽  
Carbonyl Group ◽  
Hydrogen Cyanide ◽  
Enol Form ◽  
Acid Chlorides ◽  
Trimethylsilyl Cyanide ◽  
Sterically Hindered

Abstract Fluororganic and/or sterically hindered cyanohydrines are useful synthetic reagents, not readily available directly from e.g. aldehydes or ketones and hydrogen cyanide. By using trimethylsilyl cyanide (TMSCN), the obtained O-Silyl-cyanohydrines can be applied successfully for the same purpose. Selected examples of the type R1R2C-CN(OSiMe3) 1 -12 are presented which prove the extensive applicability of this reaction [R = (fluoro)alkyl, (fluoro)aryl, anthryl, cyclopropyl, CCl3, CBr3 etc.]. Malodinitrile derivatives RC(CN)2OSiMe3 14 were obtained from carboxylic acid chlorides, α-, β- and 7 -Diketones react with formation of the corresponding linear or cyclic doubly substituted O-Silylcyanohydrines 16, 17, 21, 22. The enol-form of hexafluoroacetylacetone reacts with silylation to give the E-isomer of the silylenol ether 18, the carbonyl group of which forms the O-Silylcyanohydrine 19. With Me2Si(CN)2 both reaction steps occur intramolecular, yielding a 2,6-dioxa-l-sila-3-cyclohexene 20.

A Mild and Efficient Catalytic Strecker Reaction of N-Alkoxycarbonylamino Sulfones with Trimethylsilyl Cyanide Using Indium(III) Chloride: A Facile Synthesis of α-Aminonitriles

Synlett ◽  
2008 ◽  
Vol 2008 (20) ◽  
pp. 3133-3136 ◽  
Author(s):  
Biswanath Das ◽  
Kongara Damodar ◽  
Boddu Shashikanth ◽  
Yallamalla Srinivas ◽  
Itikala Kalavathi
Keyword(s):  
Facile Synthesis ◽  
Trimethylsilyl Cyanide ◽  
Strecker Reaction

ChemInform Abstract: A Remarkable Titanium-Catalyzed Asymmetric Strecker Reaction Using Hydrogen Cyanide at Room Temperature.

ChemInform ◽  
2011 ◽  
Vol 42 (7) ◽  
pp. no-no
Author(s):  
Balamurugan Ramalingam ◽  
Abdul Majeed Seayad ◽  
Li Chuanzhao ◽  
Marc Garland ◽  
Kazuhiko Yoshinaga ◽  
...  
Keyword(s):  
Hydrogen Cyanide ◽  
Room Temperature ◽  
Strecker Reaction
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