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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

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

Horwitz Matthew A MA Fulton Jennifer L JL Johnson Jeffrey S JS

Organic letters 20171101 21

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 contiguou ...[more]

PMID: 29035548

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