Novel catalytic kinetic resolution of racemic epoxides to allylic alcohols.

[formula: see text] The kinetic resolution of racemic epoxides via catalytic enantioselective rearrangement to allylic alcohols was investigated. Using the Li-salt of (1S,3R,4R)-3-(pyrrolidinyl)methyl-2-azabicyclo [2.2.

Asymmetric base-mediated epoxide isomerisation.

The base-mediated rearrangement of epoxides into allylic alcohols is a well-known synthetic transformation. The first enantioselective version of the reaction using a chiral base was reported in 1980. Since then, the reaction has received a lot of attention mostly due to the great usefulness of chiral allylic alcohols in organic synthesis.

New catalysts for the base-promoted isomerization of epoxides to allylic alcohols. Broadened scope and near-perfect asymmetric induction.

Optically active (1S,3R,4R)-3-[N-(trans-2,5-dialkyl)pyrrolidinyl]methyl-2-azabicyclo-[2.2.1]heptanes were evaluated as catalysts for the enantioselective beta-elimination of meso-epoxides.