Enantio- and Diastereoselective Organocatalytic Conjugate Additions of Nitroalkanes to Enone Diesters.

ABSTRACT: Enantio- and diastereoselective conjugate addition reactions between nitroethane or nitropropane and enone diesters are reported. A bifunctional triaryliminophosphorane catalyzed the addition reaction with consistently excellent stereoselectivities and yields across a wide range of substrates. By the use of the gem-diester functional handle present in the adducts, local desymmetrization via diastereotopic group discrimination was demonstrated, and a polyfunctionalized lactam with three contiguous stereocenters was synthesized.

SUBMITTER: Horwitz MA 

PROVIDER: S-EPMC5669806 | biostudies-literature | 2017 Nov

REPOSITORIES: biostudies-literature