1206188-40-0Relevant academic research and scientific papers
The asymmetric organocatalytic 1,3-dipolar cycloaddition of alkyl pyruvate-derived nitrones and α,β-unsaturated aldehydes
Weselinski, Lukasz,Kalinowska, Eleonora,Jurczak, Janusz
body text, p. 264 - 270 (2012/06/15)
The catalytic asymmetric 1,3-dipolar cycloaddition of pyruvate-derived nitrones to α,β-unsaturated aldehydes was investigated in the presence of various chiral amines. Highly functionalized isoxazolidines containing a quaternary stereocenter were obtained in moderate yields with up to 92% ee. To the best of our knowledge, this is the first example of an enantioselective 1,3-dipolar cycloaddition of ketonitrones. The model product was subsequently transformed into a 2-pyrrolidinone derivative in two steps.
Access to α-substituted amino acid derivatives via 1,3-dipolar cycloaddition of α-amino ester derived nitrones
Nguyen, Thanh Binh,Beauseigneur, Alice,Martel, Arnaud,Dhal, Robert,Laurent, Mathieu,Dujardin, Gilles
experimental part, p. 611 - 620 (2010/04/29)
(Chemical Equation Presented) Amino acid derived nitrones were conveniently synthesized in good-to-excellent yields by condensation of α-ketoesters with N-benzylhydroxylamine. The cycloaddition reactions of these nitrones with different alkenes were investigated under thermal solvent-free conditions. Considering conversions, yields, and selectivities, alkyl vinyl ethers have proven to be valuable partners to achieve this transformation, which creates a tetrafunctionalized stereogenic quaternary center. Fromthe adducts derived from vinyl ethers, a three-step access to highly functionalized α-substituted amino acid derivatives is described.
