460741-75-7Relevant academic research and scientific papers
Catalytic electronic activation: Indirect Sharpless asymmetric epoxidation of enals
Black, Phillip J.,Jenkins, Kerry,Williams, Jonathan M.J.
, p. 317 - 323 (2002)
The asymmetric epoxidation of allylic cyanohydrins using the Sharpless kinetic resolution (SKR) reaction was explored. The SKR methodology was extended to enals via in-situ conversion into the corresponding cyanohydrin. The prospect of achieving a dynamic
Kinetic resolution of racemic amino alcohols through intermolecular acetalization catalyzed by a chiral Bronsted acid
Yamanaka, Takuto,Kondoh, Azusa,Terada, Masahiro
supporting information, p. 1048 - 1051 (2015/02/19)
The kinetic resolution of racemic secondary alcohols is a fundamental method for obtaining enantiomerically enriched alcohols. Compared to esterification, which is a well-established method for this purpose, kinetic resolution through enantioselective intermolecular acetalization has not been reported to date despite the fact that the formation of acetals is widely adopted to protect hydroxy groups. By taking advantage of the thermodynamics of acetalization by the addition of alcohols to enol ethers, a highly efficient kinetic resolution of racemic amino alcohols was achieved for the first time and in a practical manner using a chiral phosphoric acid catalyst.
Exploring the versatility of the Johnson-Claisen rearrangement: access to functionally versatile δ-ethoxycarbonyl-α,β-unsaturated nitriles
Cosgrove, Kelly L.,McGeary, Ross P.
experimental part, p. 3050 - 3057 (2010/06/16)
A practical entry into δ-ethoxycarbonyl-α,β-unsaturated nitriles is described. α,β-Unsaturated aldehydes were converted to cyanohydrins, by employing either KCN in aqueous acid, or by using TMSCN with catalytic K2CO3, followed by acid hydrolysis of the TMS ether. These cyanohydrins underwent a Claisen rearrangement employing a modified Johnson-Claisen protocol to yield unsaturated nitriles in good yields and with moderate E/Z selectivity.
