ol7b02735_si_001.cif (669.14 kB)
Enantio- and Diastereoselective Organocatalytic Conjugate Additions of Nitroalkanes to Enone Diesters
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posted on 2017-10-16, 18:51 authored by Matthew
A. Horwitz, Jennifer L. Fulton, Jeffrey S. JohnsonEnantio-
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.
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nitropropaneenone diestersadductstereocenterdiastereoselective conjugate addition reactionsdesymmetrizationstereoselectivitiegemaddition reactionbifunctional triaryliminophosphoranenitroethaneDiastereoselective Organocatalytic Conjugate AdditionsEnone Diesters Enantiodiastereotopic group discriminationsubstrateNitroalkaneyieldpolyfunctionalized lactam
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