Organic Letters
Organic Letters
4 years ago

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

Enantio- and Diastereoselective Organocatalytic Conjugate Additions of Nitroalkanes to Enone Diesters
Matthew A. Horwitz, Jeffrey S. Johnson, Jennifer L. Fulton
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.

Publisher URL: http://dx.doi.org/10.1021/acs.orglett.7b02735

DOI: 10.1021/acs.orglett.7b02735

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