Enantioselective synthesis of functionalized nitrocyclopropanes by organocatalytic conjugate addition of bromonitroalkanes to alpha,beta-unsaturated enones.

doi:10.1002/chem.200801651

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Enantioselective synthesis of functionalized nitrocyclopropanes by organocatalytic conjugate addition of bromonitroalkanes to alpha,beta-unsaturated enones.

Published Jan 12, 2009 · J. Lv, Jiaming Zhang, Zhu Lin

Chemistry

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Abstract

A general enantioselective synthesis of functionalized nitrocyclopropanes by organocatalytic conjugate addition of a variety of bromonitroalkanes to alpha,beta-unsaturated enone systems is presented. The process, efficiently catalyzed by the salts of 9-amino-9-deoxyepiquinine 1 d serves as a powerful approach to the preparation of synthetically and biologically important cyclopropanes with high levels of enantio- and diastereoselectivities. Since only 0.6 equivalents of bromonitromethane are used as a reagent, (S)-2 e is obtained enantiomerically pure by employing chiral 1 d as a highly efficient catalyst for its kinetic resolution (97 % ee at 51 % conversion, selectivity s=120).

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Study Snapshot

The organocatalytic conjugate addition of bromonitroalkanes to alpha,beta-unsaturated enones efficiently catalyzes the enantioselective synthesis of functionalized nitrocyclopropanes with high enantio- and di

PopulationOlder adults (50-71 years)

Sample size24

MethodsObservational

OutcomesBody Mass Index projections

ResultsSocial networks mitigate obesity in older groups.

Enantioselective synthesis of functionalized nitrocyclopropanes by organocatalytic conjugate addition of bromonitroalkanes to alpha,beta-unsaturated enones.

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