✍ Scribed by Michael A Walker
No coin nor oath required. For personal study only.
The synthesis of iminodiacid 2, a derivative of valine, was found to be difficult at the point of attempting to functionalize the imino-nitrogen to form a tertiary amine. Nonetheless, a route was discovered starting from ¢thydroxyisovaleric acid, ethanolamine and maleimide. After esterification, the ~-triflate of o~-hydroxyisovaleric acid was formed and used to sequentially alkylate the amino group of ethanolamine. Steric hindrance was reduced by tethering two of the amine substituents into lactone ring. This was followed by maleimide substitution of the hydroxyl group under Mitsunobu conditions.
📜 SIMILAR VOLUMES
The synthesis of 2-azi-eamphane has been achieved despite the fact that the spiroeyelie carbon eente~ is sterically congested. Although the yield is somewhat low, the highly pure diazirine can be used as a precursor for the burgeoning class of sterically congested carbenes.
The reaction of Me 2 CuLi with sterically congested a,b-unsaturated esters in the presence of TMSCl in CH 2 Cl 2 proceeded very smoothly to produce the conjugate addition products in high yields.
## Abstract For Abstract see ChemInform Abstract in Full Text.