Tetrahedron p. 16575 - 16596 (1997)
Update date:2022-08-03
Topics:
Wipf, Peter
Wenjing, Xu
Hongyong, Kim
Takahashi, Hidenori
In situ prepared Cp2(CI)Zr+ catalyzes the formation of ortho esters 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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