(2R)-2-Methylpent-4-enoic acid is an organic acid with the chemical formula C6H10O2. Other names for this molecule include (R)-2-methyl-4-pentenoic acid, (R)-(−)-2-methyl-4-pentenoic acid, and methylallylacetic acid.
Synthesis (R)-2-Methylpent-4-enoic acid can be synthesized using a chiral auxiliary such an oxazolidinone derivative, popularized by David Evans. One route of synthesis consists of three steps:
acylation of the oxazolidinone using triethylamine as a base, and DMAP as an acyl carrier catalyst addition of a pentene group via enolate addition using Sodium bis(trimethylsilyl)amide as a base and allyl iodide as the pentene donor and cleavage of the oxazolidinone by LiOH solution in hydrogen peroxide. and sulfite to reduce the peroxide to the acid.
Uses (R)-2-Methylpent-4-enoic acid can also be used in synthesis of other chiral compounds. For example, it has been used in the process of synthesizing the drug Sacubitril as a reagent for adding a chiral center to the molecule.
References