Zirconocene-catalyzed epoxy ester - ortho ester rearrangement: A new method for the protection of polyfunctionalized carboxylic acids and the asymmetric synthesis of ortho esters

Add time:07/19/2019    Source:sciencedirect.com

In situ prepared Cp2(Cl)Zr⊛ catalyzes the formation of ortho eśters from epoxy esters. Acid-sensitive α-amino and α-hydroxy acid derivatives are converted in high yield to 2,7,8-trioxabicyclo[3.2.1]octanes (ABO-esters) using this protocol. This strategy is complementary to the OBO-ester technology, and orthogonal methods for the deprotection of ABO- and OBO-esters have been developed. The syntheses of the mushroom components (S)-γ-hydroxyleucine lactone and (S)-α-vinylglycine underline the value of ABO-ester protective group strategy. Using chiral epoxy alcohol derivatives, the first convenient and general asymmetric synthesis of bicyclic ortho esters has been achieved.

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