168105-12-2Relevant academic research and scientific papers
A simple asymmetric synthesis of 2-substituted 2,3-dihydro-4-pyridones
Streith, Jacques,Boiron, Arnaud,Sifferlen, Thierry,Strehler, Christiane,Tschamber, Theophile
, p. 3927 - 3930 (1994)
A pronounced asymmetric induction (d.e. = 95%) was observed during methylation of pyridinium salt 7 with MeMgI which led ultimately to (2R) 2-methyl-2,3-dihydro-4-pyridone 9. This result is best explained by assuming chelate-control during the asymmetric alkylation step.
4. Chelate-controlled asymmetric synthesis of 2-substituted 2,3-dihydropyridin-4(1H)-ones: Synthesis of D- and L-aminodeoxyaltrose derivatives
Streith,Boiron,Paillaud,Rodriguez-Perez,Strehler,Tschamber,Zehnder
, p. 61 - 72 (2007/10/02)
Asymmetric methylation and phenylation of the chiral pyridinium salt 7, as well as methylation of chiral pyridinium salt 18, with Grignard reagents occurred in good yield and with good-to-excellent diastereoselectivities. These results are best explained by assuming chelate control to govern the asymmetric alkylation/arylation process. The minimum-energy conformations of the out-of-plane twisted pyridinium salts 7 and 18, as determined hy the 'Molecular Simulations Cerius-Dreiding II' program, are in good agreement with the postulated asymmetric chelate-control mechanism.
