A new route to (+)-a-allokainic acid commencing with L-serine has been established, wherein the key step involves a C3-C4 bond formation with a simultaneous creation of a C2, C3-trans and C3, C4-trans arrangement of substituents by Rh2(0Ac)4-catalyzed C-H insertion reaction of adiazoacetoacetamide tethered to (S)-4-(3-butenyl)-2,2-dimethyl-1,3-oxazolidine system.Taher's conlputational model confirms the observed diastereomer preference.With the advent of dirhodium(l1) carboxylate catalysts, intramolecular C-H insertion reactions of adiazocarhonyl compounds, featuring C-C bond formation at an unactivated carbon atom, have been recognized as a potentially powerful means for the construction of both carbocycles, especially cyclopentanones, and heterocycles.lWhile an enormous amount of effort is being devoted to the (a) R.
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Hashimoto et al. (1999) studied this question.