Sugar‐Assisted Kinetic Resolutions in Metal/Chiral Amine Co‐Catalyzed α‐Allylations and [4+2] Cycloadditions: Highly Enantioselective Synthesis of Sugar and Chromane Derivatives

Abstract

AbstractFunctionalized triose‐, furanose and chromane‐derivatives were synthesized by the titled reactions. The sugar‐assisted kinetic resolution/C−C bond‐forming cascade processes generate a functionalized sugar derivative with a quaternary stereocenter in a highly enantioselective fashion (up to >99 % ee) by using a simple combination of metal and chiral amine co‐catalysts. Notably, the interplay between the chiral sugar substrate and the chiral amino acid derivative allowed for the construction of a functionalized sugar product with high enantioselectivity (up to 99 %) also when using a combination of racemic amine catalyst (0 % ee) and metal catalyst.